m-Chloroperbenzoic acid → 3-Chlorobenzoic Acid

Participants

Reaction Steps

m-CPBA (7.66 g, 34.18 mmol based on 77% purity) was dried in vacuum at room temperature until vacuum reached 10 mTorr. Anhydrous methylene chloride (60 mL) was added to dissolve m-CPBA. Me(MeO)2SiCH2CH═CH2 (5 g, 34.18 mmol) was added to the solution of m-CPBA in CH2Cl2. The immediate reaction was evidenced by moderate beat generation. White precipitate of m-ClC6H4COOH formed within 1 hour. The reaction mixture was left overnight. Next morning, the reaction mixture was reduced in volume under vacuum. Pentane (50 mL) was added and then the mixture was filtered. Low boiling point volatiles were removed in vacuum. The product was obtained by vacuum distillation. Yield: 40%. Boiling point 30° C. at 0.2 Torr. Mass spectrum: (El, %): m/z 162 (M+, 1), 174 (M+-Me, 10), 105 (M+-CH2CHCH2O, 100). 1H NMR (C6D6): δ 3.31 (s, 3H, SiOCH3), 3.30 (s, 3H, SiOCH3), 2.9–2.82 (m, 1H, SiCH2CHCH2O), 2.44–2.41 (m, 1H, SiCH2CHCHHO), 2.18–2.15 (m, 1H, SiCH2CHCHHO), 1.09–1.02 (m, 1H, SiCHHCHCH2O), 0.73–0.65 (m, 1H SiCHHCHCH2O), 0.08 (s, 3H, SiCH3). 13C NMR: (C6D6) δ 50.30 (SiOCH3), 50.28 (SiOCH3), 48.94 (SiCH2CHCH2O), 48.36 (SiCH2CHCH2O), 18.83 (SiCH2CHCH2O), −4.30 (SiCH3).

Provenance & Evidence