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Rosemary G. Fowler
Coney College
Nevada, M 0 64772
Experimental
Reduction of Vanillin to Vanillyl Alcohol (2)
Dissolve 380 mg (2.5 mmol) of vanillin in 2.5 mL of 1M
NaOH solution in a 25-mL Erlenmeyer flask. Swirl the
flask to obtain a yellow, homogeneous solution. Cool the
contents of the flask to between 10-15 aC by swirling the
flask in an ice-water bath. Add 75 mg (1.95 mmol) of
NaBH4in three or four portions over a period of 3 min with
(Confinued on page A l l )
Volume 69 Number 2 February 1992 A43
the microscale laboratoru
0.5-mL portions of cold water. Dry the product partially by is adapted from papers presented a t the 11th Biennial
drawing air through the crystals for several minutes. Then Conference on Chemical Education, Atlanta, GA, 1990.
transfer the product to a watch glass to air-dry.
Students typically collect 150 mg (43%yield) of the crude Literature Cited
5-bromovanillin, with a melting point of 163-164 T. Re- 1. Mayo, D. W.;Pike. R. M.; BuWler, 8.6.Mlcmsmlr Ogo- labomfory; Wiley: New
Ywk,1986.
crystallization from methanol-water yields 120 mg (35% 2. A"lt,A. Techniqu48o"dE~pimnffor O~gonieChemrstry;Au,mandBern": B o b ,
Publication Date: February 1, 1992 | doi: 10.1021/ed069pA43