Tetrahydrofuran → 4-(Hydroxymethyl)-4-(naphthalen-1-yl)cyclohexan-1-one

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Reaction Steps

A solution of 3.84 g. (0.0123 mole) of 4-carboxy-4-(1-naphthyl)cyclohexanone, ethylene ketal (prepared in Example 29) in 80 ml. of tetrahydrofuran is added to 0.5 g. (0.013 mole) of lithium aluminum hydride in 10 ml. of tetrahydrofuran. Following about 6 hours of heating at reflux the mixture is cooled in ice and treated successively with 0.5 ml. of water, 0.5 ml. of 15% sodium hydroxide solution and 1.5 ml. of water. The resulting inorganic gel is collected on a filter and rinsed with ether. The combined filtrates are evaporated to dryness to give 3.95 g. (99% yield) of 4-hydroxymethyl-4-(1-naphthyl)cyclohexanone, ethylene ketal as an amorphous gum.

Provenance & Evidence