General procedure for the synthesis of 4-methoxy-3-hydroxyacetophenone from 3'-hydroxy-4'-methoxyacetophenone (12): ketone 8 (250 mg, 1.20 mmol) was dissolved in anhydrous CH2Cl2 (3 mL), AlCl3 (208 mg, 1.56 mmol) was added, and the reaction was stirred for 24 h at 18 °C and under nitrogen protection. After completion of the reaction, the mixture was partitioned between water (10 mL) and CH2Cl2 (10 mL). The aqueous phase was extracted once with CH2Cl2 (10 mL), the organic phases were combined, dried with MgSO4, filtered and concentrated under reduced pressure. The light yellow oil obtained was purified by fast chromatography (eluent: ethyl acetate/hexane, 1:4 v/v) to give a white solid 4-methoxy-3-hydroxyacetophenone 124 (172 mg, 86% yield) with a melting point of 88.6-90.5 °C (literature value: 92-93 °C) and a TLC (silica gel plate, unfolding agent: ethyl acetate/hexane, 1:1 v/v) Rf value was 0.4. 1H NMR (300MHz, CDCl3) δ: 7.53-7.56 (m, 2H), 6.89 (d, J=7.5Hz, 1H), 5.73 (br s, 1H), 3.96 (s, 3H), 2.54 (s, 3H).
