Water → 4-(4-Hydroxymethylphenyl)cyclohexanone

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Reaction Steps

3.5 g of this product in 30 ml of pyridine are combined with 2.2 ml of thionylchloride, whilst cooling with ice. The resulting oil (2.7 g), which is a mixture of two substances, is hydrogenated in a mixture of 40 ml of ethyl acetate and 20 ml of methanol in the presence of 1.5 g of palladium/calcium carbonate at ambient temperature under a hydrogen pressure of 5 bar. The resulting oil (2.4 g) is refluxed overnight in 40 ml of acetone and 10 ml of water with 0.2 g of pyridinium-p-toluenesulphonate. The crude product is purified by column chromatography (silica gel, ethyl acetate/petroleum ether=1:1, v:v). 1.0 g of the title compound is obtained, melting point 58°-60° C.

Provenance & Evidence