Hydrochloric Acid → 4-Allyl-3,5-dihydroxy-benzoic acid methyl ester

Participants

Reaction Steps

To a solution of 4-allyl-3,5-bis-methoxymethoxy-benzoic acid methyl ester (10a) (513 mg, 1.73 mmol) in MeOH (4 mL) was added 4N HCl (4 mL). The reaction mixture was stirred at room temperature overnight. The mixture was quenched with H2O (80 mL) and extracted with EtOAc (2×80 mL). The organic layers were dried over MgSO4 and concentrated to give yellow oil which was purified by flash column chromatography eluting with 15-25% EtOAc in hexanes to give a pale yellow solid (285 mg, 79% yield). 1H NMR (400 MHz, CDCl3) δ 7.20 (s, 2 H) 5.95-6.06 (m, J=5.31, 5.31 Hz, 1 H) 5.76-5.82 (m, 2 H) 5.15-5.20 (m, 1 H) 5.12-5.15 (m, 1 H) 3.90 (s, 3 H) 3.50-3.55 (m, 2 H); LCMS for C11H12O4S m/z 209.10 (M+H+).

Provenance & Evidence