Water → HCID 4779021, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl salicylate (1.377 g, 9.05 mmol) in N,N-dimethylformamide (14 ml) were added β-bromophenetole (1.876 g, 9.33 mmol) and potassium carbonate (1.509 g, 10.91 mmol), and the mixture was stirred at 80° C. for 1.5 hr. Water was added to the reaction mixture, and the precipitated crystals were collected by filtration and washed with water and hexane to give methyl 2-(2-phenoxyethoxy)benzoate (1.545 g, 5.67 mmol, yield 63%). This was dissolved in methanol (10 ml), 2N-aqueous sodium hydroxide solution (10 ml) was added at room temperature, and the mixture was stirred at 60° C. for 3.5 hr. The reaction mixture was concentrated under reduced pressure and neutralized with 2N-aqueous hydrochloric acid solution, and the mixture was extracted with ethyl acetate. The extract was dried over sodium sulfate, and the solvent was evaporated under reduced pressure to give a carboxylic acid compound 2-(2-phenoxyethoxy)benzoic acid (1.407 g, 5.45 mmol, yield 96%).

Provenance & Evidence