Tetrahydrofuran → 4-(3,4-Dimethoxyphenyl)-4-(hydroxymethyl)cyclohexan-1-one

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Reaction Steps

A solution of 19 g. (0.059 mole) of 4-carboxy-4-(3,4-dimethoxyphenyl)cyclohexanone, ethylene ketal (prepared in Example 28) in 290 ml. of tetrahydrofuran is added to 5.35 g. (0.141 mole) lithium aluminum hydride in 80 ml. of tetrahydrofuran. Following about 6 hours of heating at reflux the mixture is cooled in ice and treated successively with 5.4 ml. of water, 5.4 ml. of 15% sodium hydroxide solution and 16.2 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 11.4 g. (62.7% yield) of 4-hydroxymethyl-4-(3,4-dimethoxyphenyl)-cyclohexanone, ethylene ketal as an amorphous gum.

Provenance & Evidence