Hydrochloric Acid → 2-(3-methyl-6-Formyl-2-carboxy-5-methoxy-phenoxy)-3,5-dimethoxy-4-methyl-benzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

2-(3-methyl-2-carboxy-5-methoxy-phenoxy)-3,5-dimethoxy-4-methyl-benzoic acid methyl ester (1 mmol) and dichloromethyl methyl ether (2 mmol) were taken in anhydrous dichloromethane (2 ml). The mixture was stirred and cooled to −10° C. in an ice-salt bath. Titanium tetrachloride (2.5 mmol) in dichloromethane (0.5 ml) was then added dropwise over 0.5 h. Stirring was continued for a further 1.5 h at −10° C. and then for 1.5 h at room temperature. To the reaction mixture was then added cold, dilute hydrochloric acid, and the reaction mixture was extracted with dichloromethane. The organic layer was washed with water, brine and then dried (MgSO4). The solvent was evaporated by a rotary evaporator and the residue was purified by column chromatography to afford 2-(3-methyl-6-Formyl-2-carboxy-5-methoxy-phenoxy)-3,5-dimethoxy-4-methyl-benzoic acid methyl ester (63%).

Provenance & Evidence