Ethylene Glycol → 1-(3,4-Dimethoxyphenyl)-4-oxocyclohexanecarboxylic Acid

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Reaction Steps

A mixture of 17.54 g. (0.058 mole) of 4-cyano-4-(3,4-dimethoxy)cyclohexanone, ethylene ketal (prepared as in Example 22) and 17.5 g. of potassium hydroxide in 175 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 19 g. (99% yield) of 4-carboxy-4-(3,4-dimethoxyphenyl)cyclohexanone, ethylene ketal, as an amorphous gum.

Provenance & Evidence