Sodium Hydroxide → 3-(4-Fluorophenyl)pentanedioic acid

Participants

Reaction Steps

An aqueous solution of sodium hydroxide (3N, 23 mL, 69 mmol) was added to a solution of 2-(4-fluorophenyl)-1,1,3-trimethoxy carbonyl propane (6.7 g, 21.5 mmol) in methanol (100 ml) at room temperature and the mixture was stirred for 12 hours. The resulting mixture was concentrated under reduced pressure, and then water (20 ml) and concentrated hydrochloric acid (10 ml) were added under ice cooling. The aqueous mixture was refluxed for 12 hours. The reaction mixture was extracted with ethyl acetate. The organic extract was washed with water and saturated sodium chloride, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was crystallized from ethyl acetate-hexane to obtain 4.5 g of 3-(4-fluorophenyl) glutaric acid (yield 93%). mp. 145–147° C.

Provenance & Evidence