monoMethyl adipate → 6-(4-Hexylphenyl)-6-oxohexanoic acid

Participants

Reaction Steps

Adipic acid monomethyl ester (50 g; 0.31 mole) is converted to the acid chloride with thionyl chloride (50 g) by the manner described in Example 1. This product is reacted with hexylbenzene (100 g) and aluminum chloride (62.4 g; 0.47 mole) and the product isolated in a manner analogous to that described in Example 1. The crude product is heated under reflux in ethanol (234 ml) and 2N sodium hydroxide (234 ml) for 4 hours. The reaction mixture is then processed as described in Example 1. The product is recrystallized from aqueous ethanol to give 5-(4-n-hexylbenzoyl)pentanoic acid as colorless crystals (22.5 g), m.p. 77°-79° C.

Provenance & Evidence