Potassium Carbonate → 3-(3-Hydroxy-propoxy)-4-methoxy-benzoic acid methyl ester

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Reaction Steps

A mixture of methyl 3-hydroxy-4-methoxybenzoate (4.94 g, 26.6 mmol), 3-bromo-1-propanol (2.86 mL, 31.9 mmol) and anhydrous K2CO3 (5.51 g, 39.9 mmol) in MeCN (50 mL) is refluxed with stirring overnight, and after cooling is poured into ice/water. The aqueous layer is extracted with AcOEt, and the combined organics are washed with brine, dried (Na2SO4) and concentrated. Purification by flash chromatography on silica gel (hexane/AcOEt 1:2) gives a solid residue which is stirred in a 9:1 mixture of hexane/AcOEt over 30 min. Filtration of the suspension and drying in vacuo gives the title compound as white solid. TLC, Rf (hexane/AcOEt 1:1)=0.09. MS: 241.2 [M+H]+. tR (HPLC, Nucleosil C18HD column, 20-100% CH3CN/H2O/6 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 1 mL/min): 2.86 min. 1H-NMR (CDCl3): δ 2.13 (m, 2H), 2.59 (m, 1H), 3.92 (s, 3H), 3.93 (s, 3H), 4.29 (m, 2H), 6.92 (m, 1H), 7.60 (s, 1H), 7.73 (m, 1H) ppm.

Provenance & Evidence