Water → Methyl 3-methoxy-5-(3-methoxypropoxy)benzoate

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-methoxy-5-hydroxybenzoic acid methyl ester (23.2 g, 127 mmol), toluene-4-sulfonic acid 3-methoxy-propyl ester (40.7 g, 167 mmol) and Kl (2.23 g, 13.4 mmol) in DMF (350 mL), K2CO3 (53.1 g, 384 mmol) is added under N2. After stirring at 60° C. for 17 h, the reaction mixture is supplemented with H2O and extracted with Et2O. The combined organic phases are washed with H2O and dried (Na2SO4). Concentration under reduced pressure and silica gel flash chromatography give the title compound as colorless oil. MS: 255 [M+H]+; tR (HPLC, CombiScreen ODS-AM 50×4.6 mm; 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 5 min then 100% CH3CN+0.1% TFA for 2 min, flow 2.0 ml/min): 3.80 min.

Provenance & Evidence