Diethyl Malonate → HCID 19363381, compound

Participants

Reaction Steps

2-bromo4-methoxy-3-pentyloxybenzoic acid (80.1 g, 253 mmol), toluene (480 ml), copper (I) bromide (3.62 g, 25.3 mmol) and diethyl malonate (153.4 ml, 1.01 mol) were mixed, and sodium hydride (60% dispersion, 30.3 g, 758 mmol) was added to this suspension. The mixture was stirred at 78° C.-83° C. for 1 hour. Said reaction mixture was combined with a reaction mixture in which 2-bromo-4-methoxy-3-pentyloxybenzoic acid (49.43 g, 156 mmol) had been reacted in the same manner, and the resulting reaction mixture was extracted with water (1000 ml, 500 ml). The aqueous layer was washed with hexane (500 ml). Concentrated hydrochloric acid was added to make the aqueous layer acidic. The aqueous layer was extracted with ethyl acetate (1000 ml, 500 ml). The organic layers were combined, and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure to give a crude product of diethyl 2-(6-carboxy-3-methoxy-2-pentyloxyphenyl)-malonate.

Provenance & Evidence