Glutaric anhydride → 5-Oxo-5-(4-pentylphenyl)pentanoic acid

Participants

Reaction Steps

Glutaric anhydride (10 g; 0.1mole) is reacted with pentylbenzene (100 ml) and aluminum chloride (29 g; 0.22 mole) at room temperature for 4 hours. The reaction mixture is poured into a mixture of ice-water (500 ml) and concentrated hydrochloric acid (50 ml) with vigorous stirring. The crude product is collected by filtration and recrystallized from aqueous ethanol to give 4-(4-n-pentylbenzoyl)butanoic acid (16.2 g) as colorless crystals, m.p. 104°-106° C.

Provenance & Evidence