Hydrochloric Acid → 3-Formyl-4-methoxy-5-trifluoromethoxybenzoic acid

Participants

Reaction Steps

To magnesium (403 mg), tetrahydrofuran (16 mL), 5-bromo-1-diethoxymethyl-2-methoxy-3-trifluoromethoxybenzene (6.19 g) and a 0.97M methylmagnesium bromide-tetrahydrofuran solution (0.42 mL) were added to the solution, and then the mixture was stirred at room temperature for 1 hour. The reaction solution was cooled to 0° C. and stirred for 45 minutes under a carbon dioxide atmosphere. 4N hydrochloric acid (25 mL) was added and then the mixture was stirred at room temperature for 30 minutes. The organic solvent was distilled off under reduced pressure and the mixture was extracted with diisopropylether. The organic layer was extracted with 1N sodium hydroxide (100 mL) added thereto and the aqueous layer was washed twice with diisopropylether. The aqueous layer was acidified with 4N hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (4.22 g) as a brown solid.

Provenance & Evidence