Ethylene Glycol → 1-(4-CHLOROPHENYL)-4-OXOCYCLOHEXANECARBOXYLIc acid

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Reaction Steps

A mixture of 21.87 g. (0.079 mole) of 4-cyano-4-(4-chlorophenyl)cyclohexanone, ethylene ketal (prepared in Example 19) and 22 g. of potassium hydroxide in 220 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 and the solid remaining is recrystallized from a mixture of ethylene chloride and Skellysolve B to give 19.26 g. (82.2% yield) of 4-carboxy-4-(4-chlorophenyl)cyclohexanone, ethylene ketal, having a melting point of 162.5° to 164.5°C.

Provenance & Evidence