Hydrochloric Acid → 3-Formyl-5-isopropyl-4-methoxybenzoic acid

Participants

Reaction Steps

To magnesium (2.43 g), tetrahydrofuran (100 mL), 5-bromo-1-diethoxymethyl-3-isopropyl-2-methoxybenzene (31.55 g) and a 0.97M methylmagnesium bromide-tetrahydrofuran solution (15 mL) were added, and then the mixture was stirred at room temperature for 2 hours. The reaction solution was cooled to 0° C. and stirred under a carbon dioxide atmosphere for 30 minutes, and then 2N hydrochloric acid (100 mL) was added and the reaction mixture was stirred at room temperature for 16 hours. The organic solvent was distilled off under reduced pressure, and then the mixture was extracted with diisopropylether. The organic layer was extracted with 1N sodium hydroxide (100 mL) added thereto, and then the aqueous layer was washed twice with diisopropylether. The aqueous layer was acidified with 4N hydrochloric acid added thereto, 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 (15.85 g) as a brown solid.

Provenance & Evidence