Methanol → Benzeneacetic acid, 3,4-dimethoxy-, methyl ester

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Reaction Steps

3,4-Dimethoxyphenylacetic acid (20 g) and concentrated sulphuric acid (1 ml) in methanol (70 ml) were stirred at reflux for 16 hours. Methanol was removed by evaporation and the residue poured into cold water (250 ml) with stirring). Extraction into ethyl acetate (2×100 ml), washing with saturated NaHCO3 (100 ml) and brine (100 ml) followed by evaporation under reduced pressure gave, as an orange oil, 3,4-dimethoxyphenylacetic acid methyl ester (18 g); NMR (DMSO-d6) 3.57(s,2H); 3.62(s,3H); 3.73(s,6H); 6.75(dd,1H); 6.88(s,1H); 6.89(d,1H).

Provenance & Evidence