Methyl 4-hydroxy-3-methoxy-5-(2-methylallyl)benzoate → Methyl 7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-carboxylate

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Reaction Steps

A solution of methyl 4-hydroxy-3-methoxy-5-(2-methylallyl)benzoate (150 g, 0.63 mol) in conc. HCl (300 mL) and MeOH (300 mL) was heated to reflux for 2 h. TLC (EtOAc/petroleum ether=1/5) showed the reaction was complete. The solution was evaporated, and the residue was extracted with EtOAc (200 mL×3). The combined organic phases were washed with brine (200 mL), dried over Na2SO4 and concentrated to give a brown oil. The crude oil was purified by column chromatography (EtOAc/petroleum ether=1/30) to give the title compound (80 g, 53%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.51 (s, 1H), 7.46 (s, 1H), 3.91 (s, 3H), 3.87 (s, 3H), 3.05 (s, 2H), 1.53 (s, 6H).

Provenance & Evidence