Methanol → 3,5-Dihydroxy-4-((E)-3-phenyl-allyl)-benzoic acid methyl ester

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Reaction Steps

To a solution of 3,5-bis-methoxymethoxy-4-((E)-3-phenyl-allyl)-benzoic acid (220 g) (18 g, 0.05 mol) in MeOH (300 mL) was added catalytic amount of conc. H2SO4 (3 mL) in one portion. The mixture was refluxed overnight. The solution was concentrated. The residue was dissolved in CH2Cl2 (75 mL) and washed with sat. NaHCO3 (25 mL). The organic layers were dried and concentrated to give a brown solid (12 g, 73% yield). 1H NMR (400 MHz, CDCl3): δ 9.63 (s, 2H), 7.11-7.34 (m, 5H), 6.93 (s, 2H), 6.32 (s, 2H), 3.77 (s, H), 3.42 (s, 2H).

Provenance & Evidence