Sodium Bicarbonate → (2RS)-2-(3,4-dichlorophenyl)-2-[(4-methoxyphenoxy)methyl]oxirane

HRID 1022594Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH2:9])=[CH:4][C:3]=1[Cl:20].C(=O)([O-])[OH:22].[Na+]>C1(C)C=CC=CC=1>[Cl:20][C:3]1[CH:4]=[C:5]([C:8]2([CH2:10][O:11][C:12]3[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=3)[CH2:9][O:22]2)[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1,2-dichloro-4-{1-[(4-methoxyphenoxy)methyl]ethenyl}benzene (15.1 g) in toluene (161 ml) was added methachloroperbenzoic acid (21.6 g), and the mixture was stirred at 60° C. for 14 hr. The reaction mixture was cooled to 0° C., and diluted with saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The obtained extract was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (5.08 g).

Workup

temperatureThe reaction mixture was cooled to 0° C.
extractionthe mixture was extracted with ethyl acetate
extractionThe obtained extract
washwas washed with brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-5779d3e3b7d147c9b0e6acec2a37d973
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722662B2

Reaction notes

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