Isophthaloyl chloride → 3-(Methoxycarbonyl)benzoic acid

참여 물질

반응 단계

A solution of 12.18 g (60 mmol) isophthaloyl chloride in 60 ml dichloromethane was added to 60 ml anhydrous methanol at 0° C. The reaction was left overnight at rt. The reaction mixture was evaporated and the residue was dissolved in dichloromethane. The organic phase was washed twice with saturated NaHCO3 aq. The dichloromethane phase was dried and evaporated. Yield 11.05 g (56.9 mmol, 95%). A solution of 11.05 g (56.9 mmol) of isophthalic acid dimethyl ester and 2.39 g (56.9 mmol) LiOH.H2O in 150 ml anhydrous methanol was stirred for 4 d at rt The solvent was evaporated and the product was dissolved in water. The aqueous phase was washed with dichloromethane. The aqueous phase was made acidic with 2 M HCl aq. The product precipitated from the aqueous phase. The product was filtered off and dried in vacuo. The product was dissolved in 200 ml dry ethanol, and thereafter 600 ml water was added slowly while stirring. The product precipitated slowly overnight at +4° C. The product was filtered and dried in vacuo. Yield 8.32 g (46.2 mmol, 81%)

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