Ethylene Glycol → 1-(4-Methoxyphenyl)-4-oxocyclohexanecarboxylic Acid

Participants

Reaction Steps

A mixture of 27.98 g. (0.103 mole) of 4-cyano-4-(4-methoxyphenyl)cyclohexanone ethylene ketal (prepared in Example 21) and 28 g. of potassium hydroxide in 280 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 methylene chloride and Skellysolve B to give 22.35 g. (83.1% yield) of 4-carboxy-4-(4-methoxyphenyl)cyclohexanone, ethylene ketal, having a melting point of 154° to 155.5°C.

Provenance & Evidence