N,N-Dimethylglycine → 3,5-Dimethoxy-2-(5-methyl-3-methoxy-phenoxy)-4-methyl-benzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 1 mmol of 2-Bromo-3,5-dimethoxy-4-methyl-benzoic acid methyl ester, 1.5 mmol of 3-methoxy-5-methylphenol, 2 mmol of Cs2CO3, 1 mmol of CuI, and 1 mmol of N,N-dimethylglycine was added to 4 mL of dioxane under nitrogen atmosphere, and then the mixture was heated to 90° C. and monitored by TLC. Upon completion, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over Na2SO4, and evaporated by a rotary evaporator. The residue was purified by column chromatography to afford 3,5-Dimethoxy-2-(5-methyl-3-methoxy-phenoxy)-4-methyl-benzoic acid methyl ester (50%): 1H NMR (DMSO-d6) δ 7.18 (s, 1H), 6.35 (s, 1H), 6.22 (t, 1H, J=2 Hz), 6.18 (bs, 1H), 3.88 (s, 3H), 3.75 (s, 6H), 3.73 (s, 3H), 2.24 (s, 3H), 2.18 (s, 3H).

Provenance & Evidence