Hydrochloric Acid → 4-Tetradecyloxybenzyl alcohol

Participants

Reaction Steps

1.35 g (36 mMols) of sodium borohydride and then 3.1 g (36 mMols) of lithium bromide were stirred into 60 ml of diethylene glycol dimethyl ether. After stirring for 30 minutes, 20.0 g (57 mMols) of 4-tetradecyloxy-benzoic acid methyl ester were added. The mixture was heated for 3.5 hours to 100° C. and poured in portions onto a mixture of 500 g of ice and 50 ml of concentrated hydrochloric acid, after which the deposit formed was filtered off and stirred with a little methylene chloride. The undissolved fraction was then filtered off and recrystallized from n-hexane. 4-tetradecyloxybenzyl alcohol melting at 73° to 75° C. was obtained in a yield of 12.5 g.

Provenance & Evidence