Hydrochloric Acid → 4-(4-Fluorophenyl)-4-(hydroxymethyl)cyclohexan-1-one

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Reaction Steps

A solution of 18.2 g. (0.065 mole) of 4-carboxy-4-(4-fluorophenyl)cyclohexanone, ethylene ketal (prepared in Example 26) in 200 ml. of tetrahydrofuran is added to 5.9 g. (0.155 mole) of lithium aluminum hydride in 50 ml. of tetrahydrofuran. Following about 6 hours of heating at reflux, the mixture is cooled in ice and treated with 10 ml. of water and 200 ml. of 2.5 N hydrochloric acid. The organic layer is washed with water and brine and then evaporated to dryness to give 18.18 g. (99% yield) of 4-hydroxymethyl-4-(4-fluorophenyl)cyclohexanone, ethylene ketal as an amorphour gum.

Provenance & Evidence