A Simple and Versatile Method for the Synthesis of Acetals from

Aldehydes and Ketones Using Bismuth Triflate

Ni chol as M. Leonard,

Matthew C. Oswal d,

Derek A. Frei berg, Bryce A. Natti er,

Russel l C. Smi th, and Ram S. Mohan*
Department of Chemistry, I llinois Wesleyan University, Bloomington, I llinois 61701
rmohan@titan.iwu.edu
Received April 15, 2002
Acetal s are obtai ned i n good yi el ds by treatment of al dehydes and ketones wi th tri al kyl orthoformate
and the correspondi ng al cohol i n the presence of 0.1 mol % Bi (OTf)
3
4H
2
O. A si mpl e procedure for
the formati on of acetal s of di aryl ketones has al so been devel oped. The conversi on of carbonyl
compounds to the correspondi ng 1,3-di oxol ane usi ng ethyl ene gl ycol i s al so catal yzed by Bi (OTf)
3

4H
2
O (1 mol %). Two methods, both of whi ch avoi d the use of benzene, have been devel oped.
Introduction
Al dehydes and ketones are frequentl y protected as
acetal s i n the course of a total synthesi s.
1a-c
I n addi ti on,
acetal s can be converted to a vari ety of other useful
functi onal groups and hence serve as useful i ntermedi -
ates i n synthesi s.
1d,e
Thus, conversi ons of carbonyl com-
pounds to the correspondi ng acycl i c and cycl i c acetal s
(1,3-di oxol anes) are i mportant syntheti c transformati ons
that have recei ved much attenti on. Acetal i zati on i s
typi cal l y carri ed out by treatment of the carbonyl com-
pound wi th the al cohol and/or the correspondi ng ortho-
formate i n the presence of an aci d catal yst. Some methods
for the formati on of di methyl acetal s i ncl ude dry HCl i n
CH
3
OH,
2
LaCl
3
/CH
3
OH/(CH
3
O)
3
CH,
3
DCC-SnCl
4
,
4
(CH
3
)
3
Si OCH
3
/Me
3
Si OTf,
5
(CH
3
O)
3
CH/p-TsOH,
6
CH
3
OH/
(CH
3
O)
4
Si /dry HCl ,
7
and CH
3
OH/PhSO
2
NHOH.
8
Fewer
methods are known for the synthesi s of di ethyl acetal s.
These i ncl ude (CH
3
CH
2
O)
3
CH/HCl ,
9
(CH
3
CH
2
O)
3
CH/
FeCl
3
i n refl uxi ng ethanol ,
10
(CH
3
CH
2
O)
3
CH/Amberl yst,
11
DDQ,
12
and ZrCl
4
.
13
The formati on of 1,3-di oxol anes
(cycl i c acetal s) i s usual l y carri ed out usi ng ethyl ene gl ycol
i n the presence of an aci d catal yst.
14
Several other
methods that do not requi re proti c aci d catal ysi s have
al so been devel oped.
15
I n addi ti on, mi l d methods for the
formati on of acetal s under al most neutral condi ti ons have
al so been devel oped.
16
The synthesi s of di al kyl acetal s
from di aryl ketones i s more di ffi cul t, and the standard
acetal i zati on condi ti ons general l y do not work wi th di aryl
ketones. Tri fl i c aci d (20 mol %) has been shown to be a
useful catal yst for synthesi s of di aryl ketones.
17
Many of
the exi sti ng methods for acetal i zati on suffer from certai n
drawbacks and often use reagents that are toxi c and
corrosi ve. For exampl e, Ti Cl
4
, BF
3
.Et
2
O, CF
3
SO
3
H, and
TMSOTF are rather corrosi ve. I n addi ti on, few of these
methods have broad appl i cabi l i ty.
Due to our conti nued i nterest i n the use of bi smuth
compounds as envi ronmental l y fri endl y reagents for
organi c synthesi s, we undertook a study of the uti l i ty of
bi smuth tri fl ate as a catal yst for acetal formati on. Herei n
we report that bi smuth tri fl ate (0.1-1.0 mol %) i s a
versati l e and robust catal yst for acetal formati on. The
hi ghl y catal yti c nature of thi s reagent and i ts wi de
appl i cabi l i ty shoul d make thi s procedure an attracti ve
al ternati ve to exi sti ng methods for acetal formati on.

Both students contri buted equal l y to the project.

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5202 J . Org. Chem. 2002, 67, 5202-5207
10.1021/jo0258249 CCC: $22.00 2002 Ameri can Chemi cal Soci ety
Publ i shed on Web 06/18/2002
Bi smuth compounds have attracted recent attenti on due
to thei r l ow toxi ci ty, l ow cost, and good shel f l i fe.
18,19
We
recentl y reported the use of bi smuth tri fl ate as a catal yst
for rearrangement of epoxi des to al dehydes and ketones,
20
formati on of acyl al s,
21
and deprotecti on of acetal s.
22
Bi smuth tri fl ate has al so been used as a catal yst for
Fri edel -Crafts acyl ati ons,
23
sul fonyl ati ons,
24
Di el s-Al der
reacti ons,
25
and aza-Di el s-Al der reacti ons.
26
Results and Discussion
Herei n we report a mi l d and general procedure for the
conversi on of al dehydes and ketones to the correspondi ng
acetal s i n good yi el ds usi ng bi smuth tri fl ate (0.1-1.0 mol
%) as a catal yst (Scheme 1). The catal yst i s very versati l e
and works wel l for the synthesi s of di methyl acetal s,
di ethyl acetal s as wel l as 1,3-di oxol anes from a vari ety
of al dehydes and ketones.
Al though bi smuth tri fl ate i s not commerci al l y avai l -
abl e, i t can be easi l y synthesi zed i n l arge quanti ti es at a
rel ati vel y l ow cost.
27
A wi de vari ety of al dehydes and
ketones underwent smooth reacti on to gi ve the corre-
spondi ng acetal i n good yi el d (Tabl e 1). The experi mental
procedure for synthesi s of acetal s i s strai ghtforward and
i nvol ves heati ng the al dehyde or ketone as a sol uti on i n
tri al kyl orthoformate (1.5 equi v) and the correspondi ng
al cohol (8 equi v) i n the presence of 0.1 mol % Bi (OTf)
3

4H
2
O. Smooth reacti on was observed at room tempera-
ture but, not surpri si ngl y, at a consi derabl y sl ower rate.
Unl i ke tri fl i c aci d or other ai r-sensi ti ve Lewi s aci ds such
as BF
3
Et
2
O or Ti Cl
4
, bi smuth tri fl ate i s a rel ati vel y
stabl e, easy to handl e sol i d that i s i nsensi ti ve to smal l
amounts of ai r and moi sture. Whi l e acetal formati on was
observed i n the presence of the catal yst and tri al ky-
l orthoformate al one, the addi ti on of the al cohol accel er-
ated the rate of the reacti on. When the reacti on was
attempted usi ng the catal yst and al cohol al one (no
tri al kyl orthoformate), si gni fi cant acetal formati on was
not observed. The addi ti on of mol ecul ar si eves or a dryi ng
agent such as anhydrous magnesi um sul fate di d not
accel erate the reacti on si gni fi cantl y. Aromati c al dehydes
wi th both acti vati ng and deacti vati ng groups (entri es
1-4), conjugated al dehydes (entri es 5 and 6), and al i -
phati c al dehydes (entri es 7 and 8) underwent smooth
transformati on to the correspondi ng acetal i n good yi el d.
I n al most al l cases, the crude product was found to be
>98% pure (determi ned by GC and
1
H and
13
C NMR).
Commerci al ci tral (entry 6), avai l abl e as a mi xture of E/ Z
i somers, was subjected to the reacti on condi ti ons and, i t
was found that the doubl e bond i n ci tral di d not undergo
i someri zati on duri ng acetal formati on. Thi s i ndi cates that
the reacti on condi ti ons are rel ati vel y mi l d and not
suffi ci entl y aci di c to cause i someri zati on of the doubl e
bond. The conversi on of ketones (entri es 9-11) to the
correspondi ng acetal was al so successful l y carri ed out.
Whi l e a l arge number of methods exi st for synthesi s of
di methyl acetal s, fewer methods are avai l abl e for syn-
thesi s of di ethyl acetal s. One reported method that i s
catal yti c i n nature uses DDQ as the catal yst.
12
DDQ,
however, i s rather toxi c and corrosi ve, and hence i t i s
desi rabl e to have safer al ternati ves. Usi ng bi smuth
tri fl ate as a catal yst (0.1 mol %), we were abl e to
synthesi ze a vari ety of di ethyl acetal s (entri es 12-16) i n
good yi el ds. The best yi el ds were obtai ned usi ng 2.4 equi v
of tri ethyl orthoformate and 6.2 equi v of ethanol .
Di aryl ketones are qui te resi stant to the standard
condi ti ons for acetal i zati on, and hence i ndi rect routes to
thei r preparati on have been devel oped. For exampl e, the
di methyl acetal s of 4,4-di chl orobenzophenone and 4,4-
di methoxybenzophenone have been prepared by al koxy-
hal ogen exchange from the correspondi ng di hal odi aryl -
methanes.
28
To study the versati l i ty of bi smuth tri fl ate,
we extended our methodol ogy to a seri es of benzophe-
nones (Tabl e 2). Grati fyi ngl y, the correspondi ng acetal s
were obtai ned i n excel l ent yi el ds wi th onl y 1.0 mol %
bi smuth tri fl ate. When the substi tuted benzophenones
were i nsol ubl e i n methanol /tri methyl orthoformate, ni -
tromethane was used as a cosol vent. A wi de vari ety of
substi tuted benzophenones underwent smooth reacti on
to gi ve both di methyl and di ethyl acetal s. However,
fl uorenone (entry 7) fai l ed to gi ve the correspondi ng
acetal . I t has been reported that even wi th 20 mol %
tri fl i c aci d as a catal yst, the acetal i zati on of fl uorenone
was not successful .
17
The standard method for synthesi s of 1,3-di oxol anes
consi sts of heati ng a mi xture of the carbonyl compound
(18) (a) Regl i nski , J. I n Chemistry of Arsenic, Antimony and
Bismuth; Norman, N. C., Ed.; Bl acki e Academi c and Professi onal : New
York, 1998; pp 403-440. (b) Marshal l , J. A. Chemtracts 1997, 1064-
1075. (c) Suzuki , H.; I kegami , T.; Matano, Y. Synthesis 1997, 249.
(19) Organobismuth Chemistry; Suzuki , H.; Matano. Y., Eds.;
El sevi er: Amsterdam, 2001.
(20) Bhati a, K. A.; Eash, K. J.; Leonard, N. M.; Oswal d, M. C.;
Mohan, R. S. Tetrahedron Lett. 2001, 42, 8129.
(21) Carri gan, M. D.; Eash, K. J.; Oswal d, M. C.; Mohan, R. S.
Tetrahedron Lett. 2001, 42, 8133.
(22) Wi el and, L. C.; Carri gan, M. C.; Sarapa, D.; Smi th, R. S.;
Mohan, R. S. J . Org. Chem. 2002, 67, 1027.
(23) (a) Labroui l l e`re, M.; Le Roux, C.; Gaspard, H.; Laporteri e, A.;
Dubac, J. Tetrahedron Lett. 1997, 38, 8871. (b) Repi chet, S.; Le Roux,
C.; Dubac, J.; Desmurs, J. R. Eur. J . Org. Chem. 1998, 2743.
(24) Repi chet, S.; Le Roux, C.; Hernandez, P.; Dubac, J. J . Org.
Chem. 1999, 64, 6479.
(25) (a) Garri gues, B.; Gonzaga, F.; Robert, H.; Dubac, J. J . Org.
Chem. 1997, 62, 4880. (b) Robert, H.; Garri gues, B.; Dubac, J.
Tetrahedron Lett. 1998, 39, 1161.
(26) Laurent-Robert, H.; Garri gues, B.; Dubac, J. Synlett 2000, 1160.
(27) Labroui l l e`re, M.; Le Roux, C.; Gaspard, H.; Laporteri e, A.;
Dubac, J.; Desmurs, J. R. Tetrahedron Lett. 1999, 40, 285. Bi smuth
tri fl ate synthesi zed by thi s procedure i s reported to be mai nl y the
tetrahydrate. Recentl y, another procedure for the synthesi s of bi smuth
tri fl ate has been reported. Repi chet, S.; Zwi ck, A.; Vendi er, L.; Le Roux,
C.; Dubac, J. Tetrahedron Lett. 2002, 43. 993.
(28) Hardi e, W. R.; Hi dal go, J.; Hal verstadt.; Al l en, R. E. J . Med.
Chem. 1966, 9, 127.
SCHEME 1
Synthesis of Acetals fromAldehydes and Ketones
J . Org. Chem, Vol. 67, No. 15, 2002 5203
TABLE 1. Formation of Acyclic Acetals fromAldehydes and Ketones Using Bi(OTf)34H2O
a
Superscri pted numbers accompanyi ng entry numbers refer to l i terature references for the product.
b
Al l reacti ons were carri ed out at
refl ux temperatures unl ess otherwi se menti oned.
c
Refers to the yi el d of the i sol ated product. The crude product was esti mated to be
g98% pure unl ess otherwi se menti oned.
d
Product i s commerci al l y avai l abl e.
e
Puri fi ed by fl ash chromatography.
f
Contai ns 5% SM.
g
Contai ns 2% tri ethyl orthoformate.
h
Contai ns 5% tri ethyl orthoformate.
i
Puri fi ed by Kugel rohr di sti l l ati on.
Leonard et al .
5204 J . Org. Chem., Vol. 67, No. 15, 2002
i n ethyl ene gl ycol and removi ng the water as an azeo-
trope wi th benzene. Thi s method i s not parti cul arl y
sui tabl e for smal l -scal e synthesi s and al so uses the
carci nogeni c sol vent benzene. We have devel oped two
practi cal methods for the synthesi s of 1,3-di oxol anes
(Tabl e 3). I n one method (method A), tol uene i s used as
a sol vent and 1.0 mol % Bi (OTf)
3
4H
2
O serves as the
catal yst. Under these condi ti ons, at 110 C, the reacti ons
reached >95% conversi on and the pure di oxol ane was
then i sol ated by fl ash chromatography. The advantage
of thi s method i s that no Dean-Stark trap i s needed,
maki ng the procedure sui tabl e for smal l -scal e reacti ons.
A search for a substi tute for the hi ghl y toxi c sol vent
benzene l ed to fl uorobenzene (whi ch, unl i ke benzene, i s
not cl assi fi ed as a carci nogen) as the sol vent of choi ce
for removal of the water formed as an azeotrope (method
B). Agai n the reacti on was catal yzed by as l i ttl e as 1.0
mol % Bi (OTf)
3
4H
2
O. As i n the synthesi s of di al kyl
acetal s, the addi ti on of mol ecul ar si eves di d not i ncrease
the percent conversi on or yi el d.
Conclusions
Bi smuth tri fl ate (0.1-1.0 mol %) has been shown to
be a versati l e and robust catal yst for the synthesi s of
di methyl and di ethyl acetal s as wel l as 1,3-di oxol anes
from a wi de vari ety of al dehydes and ketones. The
procedure al so works very wel l wi th di aryl ketones, whi ch
are often resi stant to the standard acetal i zati on condi -
ti ons. The hi ghl y catal yti c nature of thi s reagent coupl ed
wi th i ts l ow cost, noncorrosi ve nature, ease of handl i ng,
and wi de appl i cabi l i ty shoul d make thi s method for
synthesi s of acetal s parti cul arl y attracti ve.
Experimental Section
Methanol was dri ed over magnesi um metal .
29
Fl uoroben-
zene, tri methyl orthoformate, and tri ethyl orthoformate were
(29) (a) Lund, H.; Bjerrum, J. Berichte1931, 64, 210. (b) Lund, H.
Berichte1934, 37, 936. (c) Lund, H. J . Am. Chem. Soc. 1952, 74, 3188.
(30) Luche, J.-L.; Gemal , A. L. J . Chem. Soc. Chem. Commun. 1978,
976.
(31) Heywood, D. L.; Phi l l i ps, B. J . Org. Chem. 1960, 25, 1699.
(32) Yamato, M.; Hashi gaki , K.; Kokubu, N.; Tashi ro, T.; Tsuruo,
T. J . Med. Chem. 1986, 29, 1202.
(33) Reddy, B. M.; Reddy, V. R.; Gi ri dhar, D. Synth. Commun. 2001,
31, 1819.
(34) Suzuki , T.; Ori yama, T. Synth. Commun. 1999, 29, 1263.
(35) Wang, W.-B.; Shi , L.-L.; Huang, Y.-Z. Tetrahedron Lett. 1990,
46, 3315.
(36) Carbera, A.; Vazquez, D.; Vel asco, L.; Sal mon, M.; Ari as, J. L.
J . Mol. Catal. 1992, 75, 101.
(37) Gi hani , M. E.; Heaney, H. Synlett 1993, 583.
TABLE 2. Formation of Acyclic Acetals fromDiaryl Ketones Using Bi(OTf)34H2O
a
Superscri pted numbers agai nst entry numbers refer to l i terature references for the product.
b
Al l reacti ons were carri ed out at refl ux
temperature.
c
Refers to the yi el d of crude product unl ess otherwi se menti oned. Puri ty of the crude product was esti mated to be g98% by
1
H and
13
C NMR spectroscopy.
d
Ni tromethane was used a cosol vent.
e
Puri fi ed by fl ash chromatography.
Synthesis of Acetals fromAldehydes and Ketones
J . Org. Chem, Vol. 67, No. 15, 2002 5205
used as recei ved. Ethyl ene gl ycol was dri ed over 4 si eves
before use. Commerci al l y avai l abl e 200 proof ethanol was dri ed
over anhydrous magnesi um sul fate pri or to use. Reacti ons
were heated at the i ndi cated temperature usi ng a temperature-
control l ed oi l bath.
RepresentativeProcedurefor Synthesis of Dimethyl
and Diethyl Acetals. A sol uti on of p-chl orobenzal dehyde
(3.00 g, 21.3 mmol ) and tri methyl orthoformate (3.39 g, 31.95
mmol ) i n methanol (7.0 mL) was sti rred as bi smuth tri fl ate
(14.0 mg, 0.0213 mmol , 0.1 mol %) was added. The resul ti ng
mi xture was heated at refl ux for 3 h and then cool ed to room
temperature. Saturated aqueous NaHCO
3 (20 mL) was added,
and the mi xture was sti rred wel l and extracted wi th ether (2
20 mL). The combi ned organi c l ayers were washed wi th
water (3 15 mL) and saturated aqueous NaCl (15 mL). The
organi c l ayer was dri ed (Na2SO4), and the sol vents were
removed on a rotary evaporator to yi el d 3.56 g (89%) of a
col orl ess oi l (>99% pure by GC and
1
H and
13
C NMR) that
was i denti fi ed as the correspondi ng di methyl acetal by
1
H and
13
C NMR spectroscopy.
Representative Procedure for Synthesis of Acetals
fromDiaryl Ketones. A mi xture of 4,4-di fl uorobenzophenone
(1.00 g, 4.58 mmol ) i n methanol (3 mL) and tri methyl ortho-
formate (3.16 g, 3.3 mL, 29.8 mmol ) was sti rred at room
temperature as bi smuth tri fl ate (30 mg, 0.0458 mmol , 1.0 mol
%) was added. As the mi xture was heated, a sol uti on resul ted (38) Fadel , A.; Yefsah, R.; Sal aun, J. Synthesis 1987, 37.
TABLE 3. Formation of 1,3-Dioxolanes fromAldehydes and Ketones
a
Superscri pted numbers agai nst entry numbers refer to l i terature references for the product.
b
Determi ned by GC anal ysi s of the
reacti on mi xture.
c
Refers to the yi el d of pure (g98%), i sol ated product after puri fi cati on by fl ash chromatography.
d
Rel ati ve to the al dehyde,
2 equi v of 2,2-di methoxypropane was added as a water scavenger.
e
Product was found to be g98%pure by
1
H and
13
C NMR. GC anal ysi s,
however, showed the product to be 90% pure.
f
Product i s commerci al l y avai l abl e.
Leonard et al .
5206 J . Org. Chem., Vol. 67, No. 15, 2002
that was further heated at refl ux for 24 h and al l owed to cool
to room temperature. The sol uti on was then poured onto 10%
aqueous NaHCO3 (15 mL), whi ch resul ted i n preci pi tati on of
a sol i d. The mi xture was cool ed i n i ce, and the sol i d formed
was col l ected by sucti on fi l trati on and dri ed i n a vacuum
desi ccator to afford 1.14 g (94%) of whi te crystal s. The product
has been reported i n the l i terature, but
13
C NMR data has not
been previ ousl y reported:
13
C NMR (67.5 MHz, CDCl 3) 49.2,
102.2, 114.8 (d, J CF ) 21.1 Hz), 128.7 (d, J CF ) 8.3 Hz), 138.19
(d, J CF ) 3.1 Hz), 162.2 (d, J CF ) 244.9 Hz).
Dimethyl Acetal of 4-Nitrobenzophenone. A mi xture of
4-ni trobenzophenone (2.00 g, 8.80 mmol ) i n methanol (4.5 g,
5.7 mL, 0.141 mol ) and tri methyl orthoformate (6.07 g, 6.3 mL,
57.2 mmol ) was sti rred at room temperature as bi smuth
tri fl ate (57.8 mg, 0.0880 mmol , 1.0 mol %) was added. The
resul ti ng mi xture was heated at refl ux, and ni tromethane (5
mL) was added unti l a sol uti on resul ted. The sol uti on was
refl uxed for 24 h and al l owed to cool to room temperature. I t
was then poured onto 10%aqueous NaHCO
3 sol uti on (15 mL),
and the mi xture was extracted wi th CH2Cl 2 (2 20 mL). The
combi ned organi c l ayers were washed wi th H2O (2 15 mL)
and saturated NaCl (15 mL), dri ed (Na2SO4), and concentrated
on a rotary evaporator to gi ve 2.00 g (83%) of off-whi te
crystal s: I R (KBr) 2967, 2834, 1559, 1343, 1212, 1090 cm
-1
;
1
H NMR (270 MHz, CDCl 3) 3.13 (s, 6 H), 7.24 (m, 3 H), 7.45
(m, 2 H), 7.67 (m, 2 H), 8.4 (m, 2 H);
13
C NMR 49.3, 102.1,
123.2, 126.6, 127.8, 127.9, 128.2, 140.8, 147.1, 149.5; mp 61-
63 C. Anal . Cal cd. for C15H15NO2: C, 65.92; H, 5.53; N, 5.13.
Found: C, 65.84; H, 5.55; N, 5.17.
Synthesis of 1,3-Dioxolanes (Method A). A mi xture of
p-chl orobenzal dehyde (3.00 g, 21.34 mmol ), ethyl ene gl ycol
(5.30 g, 85.4 mmol ), and tol uene (6 mL) was sti rred at room
temperature as Bi (OTf)34H2O (0.140 g, 0.213 mmol , 1.0 mol
%) was added. The mi xture was heated under N2 at 110 C i n
an oi l bath. After 4.5 h, the mi xture was poured onto 10%
aqueous NaHCO3 (25 mL) and extracted wi th ether (45 mL).
The organi c l ayer was then washed wi th H2O (4 30 mL),
saturated NaCl (30 mL), dri ed (Na2SO4), and concentrated on
a rotary evaporator to yi el d 3.72 g of an oi l that was puri fi ed
by fl ash chromatography on 300 g of si l i ca to yi el d 2.83 g (72%)
of a cl ear l i qui d that was consi stent wi th the expected
di oxol ane (>98% pure as confi rmed by GC anal ysi s and
1
H
and
13
C NMR spectroscopy).
Synthesisof 1,3-Dioxolanes(MethodB). A round-bottom
fl ask was charged wi th p-chl orobenzal dehyde (3.00 g, 21.34
mmol ), fl uorobenzene (10 mL), ethyl ene gl ycol (10.60 g, 0.171
mol ), and bi smuth tri fl ate (0.140 g, 0.213 mmol , 1.0 mol %).
The fl ask was equi pped wi th a Dean-Stark trap, and the wel l -
sti rred mi xture was heated at 110 C usi ng an oi l bath. After
5 h, the mi xture was poured on to 10% aqueous NaHCO
3
sol uti on (30 mL) and extracted wi th ether (3 40 mL). The
organi c l ayer was then washed wi th H2O (4 30 mL) and
saturated NaCl (30 mL), dri ed, and concentrated on a rotary
evaporator to yi el d 3.00 g (76%) of a col orl ess oi l that was
consi stent wi th the expected di oxol ane (>98% pure as con-
fi rmed by GC and
1
H and
13
C NMR spectroscopy).
Acknowledgment. We thank the Nati onal Sci ence
Foundati on for an RUI grant. R.M. al so thanks The
Cami l l e and Henry Dreyfus Foundati on for a teacher-
schol ar award.
JO0258249
Synthesis of Acetals fromAldehydes and Ketones
J . Org. Chem, Vol. 67, No. 15, 2002 5207