m-Chloroperbenzoic acid → 3-Chlorobenzoic Acid

HRID 1794625Notes

Reaction equation

HRID 1794625 reaction equation
[CH:1]1[CH:6]=[C:5]([Cl:7])[CH:4]=[C:3]([C:8]([O:10]O)=[O:9])[CH:2]=1>C(Cl)Cl>[Cl:7][C:5]1[CH:4]=[C:3]([C:8]([OH:10])=[O:9])[CH:2]=[CH:1][CH:6]=1

Participants

3

Reactant 1

HCID 70297m-Chloroperbenzoic acid3×

Product 1

HCID 4473-Chlorobenzoic AcidYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  1. customThe immediate reaction

Sources & evidence

ORD record
ord-c1ab30eddc0f4efba1d25e131d0ace04
Source dataset
uspto-grants-2006_04
Patent number
US07022864B2

Reaction notes

Loading…