Triethylamine → 4-(Methoxycarbonyl)-2,6-dimethylbenzoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of trifluoromethanesulfonic acid, 4-(methoxycarbonyl)-2,6-dimethylphenyl ester (3.12 g, 10 mmol) in acetonitrile (80 mL) and water (10 mL) at 25° C. is added palladium (II) acetate (224.5 mg, 1.0 mmol), 1,3-bis(diphenylphosphino)propane (412.5 mg, 10 mmol), followed by triethylamine (2.79 mL, 20 mmol). The reaction is then pressurized to 40 psi with carbon monoxide and heated to 80° C. for 4 h. The mixture is diluted with ethyl acetate (500 mL) and is washed with water (250 mL) containing 5 mL of triethylamine. The separated aqueous layer is re-extracted with ethyl acetate (2×250 mL) and the combined organic layers are discarded. The aqueous phase is then adjusted with 1N hydrochloric acid solution to pH 2 and is extracted with ethyl acetate (500 mL). The organic extract is washed with water (250 mL) and brine (250 mL), then is dried (MgSO4), filtered and evaporated in vacuo to yield 2,6-dimethyl-4-(methoxycarbonyl)benzoic acid.

Provenance & Evidence