Ethylene Glycol → 4-Oxo-1-phenylcyclohexane-1-carboxylic acid

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Reaction Steps

A mixture of 11.27 g. (0.046 mole) of 4-cyano-4-phenylcyclohexanone, ethylene ketal (prepared in Example 18) and 11.3 g. of potassium hydroxide in 90 ml. of ethylene glycol is heated at reflux for about 16 hours. The resulting solution is allowed to cool, diluted with water and washed with ether. The aqueous layer was covered with ether and then cautiously acidified. The aqueous layer is extracted with two additional portions of ether and the extracts combined. The extracts are evaporated to dryness and the solid remaining is recrystallized from a mixture of ethylene chloride and Skellysolve B to give 10.51 g. (86.3% yield) of 4-carboxy-4-phenylcyclohexanone, ethylene ketal, having a melting point of 136° to 140°C.

Provenance & Evidence