Potassium Carbonate → 3,5-Dimethoxy-4-(2-morpholin-4-yl ethoxy)benzoic acid methyl ester

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Reaction Steps

To a solution of methyl 3,5-dimethoxy-4-hydroxybenzoate (3.0 g, 14 mmol) in DMF (10 mL) was added 4-(2-chloroethyl)-morpholine hydrochloride (3.99 g, 21 mmol) and solid K2CO3 (8.4 g, 60 mmol). The mixture was heated at 60 C under N2 for 30 h. Diluted with EtOAc (100 mL) and washed with H20 (2×50 mL), back extracted the aqueous phase, and washed combined organics with brine. Dried over Na2SO4, filtered and evaporated to give the product as a brown solid (4.79 g, quantitative). 1H-NMR (CDCl3, 500 MHz 7.28 (s, 2H), 4.15 (t, 2H), 3.91 (s, 3H), 3.88 (s, 6H), 3.75-3.71 (m, 4H), 2.78 (t, 2H), 2.59 (br s, 4H) ppm; MS (FIA) 326.17 (M+H)

Provenance & Evidence