Ethylene Glycol → 1-(4-Fluorophenyl)-4-oxocyclohexanecarboxylic acid

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Reaction Steps

A mixture of 18.17 g. (0.07 mole) of 4-cyano-4-(4-fluorophenyl)cyclohexanone, ethylene ketal (prepared in Example 20 and 15 g. of potassium hydroxide in 150 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 is 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 to give 18.2 g. (93% yield) of 4-carboxy-4-(4-fluorophenyl)cyclohexanone, ethylene ketal, having a melting point of 117° to 122°C.

Provenance & Evidence