Hydrochloric Acid → 5-(4-Chlorophenyl)-5-oxopentanoic acid

Participants

Reaction Steps

To a stirred solution of aluminium bromide (300 g, 1.12 mol) in dry chlorobenzene (700 ml) at 4° C. was added a solution of glutaric anhydride (60 g, 0.526 mol) in chlorobenzene (300 ml). The resulting orange/yellow suspension was allowed to warm to RT, stirred overnight, then carefully poured into an ice cold stirred solution of 10% HCl (aqueous 1400 ml). The resulting white suspension was poured into EtOAc (900 ml) and the layers separated. The aqueous layer was washed with EtOAc (2×250 ml). The combined organic layer was washed with brine (1×400 ml), dried (MgSO4) and the solvent removed in vacuo to give a yellow/white solid (115.74 g). Recrystallization from toluene/hexane (2:1, 750 ml) gave the title compound (95.14 g) as off white crystals.

Provenance & Evidence