m-Chloroperbenzoic acid → Methyl 2-phenyloxirane-2-carboxylate
Reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[CH2:5].C1C=C(Cl)C=C(C(OO)=[O:21])C=1>C(Cl)Cl>[CH3:1][O:2][C:3]([C:4]1([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:5][O:21]1)=[O:12]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 45 °C
Procedure
The title compound was synthesized according to a literature method (Whitman Tetrahedron 1985, 41, 1183). To a mixture of 2-phenylacrylic acid methyl ester (7.92 g, 45 mmol) in 60 ml of methylene chloride was added mCPBA (13.1 g, 58.5 mmol) and the reaction was stirred at 45° C. overnight. The reaction mixture was then filtered and the solid was washed with methylene chloride. The filtrate was washed three times with 50 ml of equal parts solution consisting of saturated Na2S2O3 and saturated NaHCO3. The organic layer was washed with water and brine, dried over MgSO4, and concentrated under reduced pressure to afford the title compound in greater than 95% purity according to 1H NMR (85% yield). 1H NMR (CDCl3, 300 MHz) δ: 7.50-7.30 (m, 5H), 4.22 (q, J=7.2 Hz, 2H), 3.40 (d, J,=7.1 Hz, 1H), 2.95 (d, J=7.1 Hz, 1H), 1.26 (t, J=7.2 Hz, 3H) ppm.
Workup
- customThe title compound was synthesized
- filtrationThe reaction mixture was then filtered
- washthe solid was washed with methylene chloride
- washThe filtrate was washed three times with 50 ml of equal parts solution
- washThe organic layer was washed with water and brine
- dry with materialdried over MgSO4
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-46764ac44eeb423e97af8d2be89458ee
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08143375B2
Reaction notes
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