Water → 4-[(2-Methylquinolin-4-yl)methoxy]benzoic acid

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Reaction Steps

2.3 ml (18.6 mmol) of an 8N aqueous solution of sodium hydroxide and 5 ml of water are added to a solution of 3.6 g (9.3 mmol) of benzyl 4-(2-methylquinolin-4-ylmethoxy)benzoate diluted in 20 ml of tetrahydrofuran and 30 ml of methanol. The reaction medium is stirred at ambient temperature for 48 h then 1 ml of an 8N aqueous solution of sodium hydroxide is added and the mixture is heated at 70° C. for 5 h. After evaporation of the tetrahydrofuran, water and a 1N aqueous solution of acetic acid are added. The suspension is stirred overnight at ambient temperature then filtered. The solid obtained is dried under vacuum at 40° C. for 6 h. 2.2 g (81%) of 4-(2-methylquinolin-4-ylmethoxy)benzoic acid are obtained in the form of a white solid.

Provenance & Evidence