m-Chloroperbenzoic acid → HCID 86745361, compound

HRID 1461752Notes

Reaction equation

HRID 1461752 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]1([CH:18]=[CH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH2:26][C:27]([O:29][CH3:30])=[O:28])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(Cl)Cl>[C:12]1([C@@H:18]2[O:9][C@H:19]2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH2:26][C:27]([O:29][CH3:30])=[O:28])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 54015926HCID 54015926, compound

Product 1

HCID 86745361HCID 86745361, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7.8 g of m-chloroperbenzoic acid (about 50% pure) are added to a solution of 6 g of methyl 2-(2-phenylethenyl)phenylacetate (E/Z=3:1) in 50 ml of methylene chloride. The reaction mixture is refluxed for 12 hours and then the precipitate is filtered off with suction and the filtrate is washed twice with saturated sodium bicarbonate solution and water. The isolated organic phase is dried over sodium sulfate and concentrated, and the residue is recrystallized from methyl tert-butyl ether. 3.1 g (48%) of methyl trans-2-(3-phenyl-2-oxiranyl)phenylacetate are obtained of melting point 118°-119° C. Chromatography of the mother liquor on silica gel (6:1 ethyl acetate/n-hexane) yields 2.8 g (44%) of methyl 2-(3-phenyl-2-oxiranyl)phenylacetate as a 1:1 cis/trans mixture.

Workup

  1. temperatureThe reaction mixture is refluxed for 12 hours
  2. filtrationthe precipitate is filtered off with suction
  3. washthe filtrate is washed twice with saturated sodium bicarbonate solution and water
  4. dry with materialThe isolated organic phase is dried over sodium sulfate
  5. concentrationconcentrated
  6. customthe residue is recrystallized from methyl tert-butyl ether

Sources & evidence

ORD record
ord-a3f0feb1144540f8917c825071b42d43
Source dataset
uspto-grants-1991_12
Patent number
US05077303

Reaction notes

Loading…