Hydrochloric Acid → Benzoic acid, 2-[(carboxymethyl)methylamino]-5-methoxy-

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Reaction Steps

A mixture of 244 g (0.91 mole) of the potassium salt of 2-bromo-5-methoxybenzoic acid (prepared by treating a solution of the parent carboxylic acid in 2-propanol with excess methanolic potassium hydroxide), 196 g (1.54 mole) of the potassium salt of N-methylglycine (prepared as above), 13 g (0.82 mole) of anhydrous potassium carbonate and 0.66 g (0.01 mole) of copper powder in 220 ml of water was stirred at reflux for five hours. The mixture was cooled, added to 4.0 kg of ice/water, and acidified with concentrated hydrochloric acid to precipitate the crude product. THe solid was filtered and washed with water to yield 186 g (86% yield) of the carboxylic acid product. A sample recrystallized from aqueous 2-methoxyethanol was analytically pure, mp 196° C.-dec.

Provenance & Evidence