Ammonium Chloride → HCID 68121721, compound

Participants

Reaction Steps

A solution of 3.0 grams of 4 (2,2-dimethyl-1,1-ethylenedioxypropyl)-acetophenone in 150 ml. tetrahydrofuran is placed in a 250 ml. flask fitted with a dropping funnel and a magnetic stirring bar. Ten milliliters of a 70% solution of sodium bis-(2-methoxyethoxy)-aluminum hydride in benzene is placed in the dropping funnel. The solution is added over 30 minutes, and after the addition is complete, the mixture is stirred for 30 minutes, following which it is poured onto 100 grams of crushed ice to which 50 ml. of saturated ammonium chloride solution has been added. The organic phase is separated and the aqueous phase is extracted thrice with chloroform. The extracts are added to the organic phase, and the combined organic material is dried over anhydrous potassium carbonate. The drying agent is filtered off and the solvent is removed from the filtrate under reduced pressure on a rotary evaporator. The resulting oil is purified by column chromatography using silica gel as the support and benzene as the eluant to give 4-(2,2-dimethyl-1,1-ethylenedioxypropyl)-α-methylbenzyl alcohol, (m.p. 67°-70° C.)

Provenance & Evidence