Hydrochloric Acid → 5-(2-Methylphenyl)-5-oxovaleric acid

Participants

Reaction Conditions

Reaction Steps

A stirred solution of glutaric anhydride (22.82 g) in dry tetrahydrofuran (300 mL) at −78° C. is treated with a solution of 2-methylphenyl magnesium chloride in tetrahydrofuran (200 mL, 0.1 M) over 45 minutes. The mixture is stirred at −78° C. for 2.5 hours and the grey suspension is poured into 1 N hydrochloric acid (300 mL). The mixture is extracted with ethyl acetate (300 mL). The organic phase is dried over magnesium sulphate and evaporated to give 5-oxo-5-(2-methylphenyl)pentanoic acid (36.74 g) as a red-brown oil.

Provenance & Evidence