m-Chloroperbenzoic acid → HCID 86745362, compound

HRID 1461753Notes

Reaction equation

HRID 1461753 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[C:26](=[CH:31][O:32][CH3:33])[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[C:26](=[CH:31][O:32][CH3:33])[C:27]([O:29][CH3:30])=[O:28])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 128391HCID 128391, compound

Product 1

HCID 86745362HCID 86745362, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7.2 g of m-chloroperbenzoic acid (about 50% pure) are added to a solution of 10.2 g of methyl 2-[2-(2-phenylethenyl)phenyl]-3-methoxyacrylate in 80 ml of methylene chloride. The reaction mixture is refluxed for two days 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. 6.2 g (58%) of methyl trans-2-[2-(3-phenyl-2-oxiranyl)phenyl]-3-methoxyacrylate are obtained of melting point 110°-113° C.

Workup

  1. temperatureThe reaction mixture is refluxed for two days
  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-b865bce70ba94ac6bc87c03916deb9e5
Source dataset
uspto-grants-1991_12
Patent number
US05077303

Reaction notes

Loading…