32194-76-6

a) Synthesis of 3-(methoxymethyl)benzoic acid: Sodium methanol (0.74 g, 13.8 mmol) was added to a solution of methyl 3-bromomethylbenzoate (1129-28-8, 1.05 g, 4.6 mmol) in anhydrous methanol (30 mL) under argon protection and room temperature. The resulting suspension was stirred and reacted at 50 °C for 2 h. Subsequently, 5 M aqueous potassium hydroxide solution was added and stirring was continued for 1.5 h at 50 °C. The reaction mixture was cooled to room temperature and the pH was adjusted to 2-3 with aqueous hydrochloric acid.The aqueous phase was extracted with ethyl acetate, the organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give the target product 3-(methoxymethyl)benzoic acid as a colorless oil (749 mg, 96% yield).LCMS analysis: retention time RtB = 2.47 min; [M + H]+ = 167.0.

[1] Patent: US2012/101110, 2012, A1. Location in patent: Page/Page column 70
[2] Patent: US2012/165331, 2012, A1. Location in patent: Page/Page column 27-28
[3] Patent: WO2012/101487, 2012, A1. Location in patent: Page/Page column 65; 66