m-Chloroperbenzoic acid → HCID 13066718, compound

HRID 1164115Notes

Reaction equation

HRID 1164115 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][CH:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[C:21]([S:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:29])[C:16]=2[O:15][C:14]1=[O:30]>C(Cl)(Cl)Cl>[CH3:12][CH:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[C:21]([S:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:29])=[O:9])[C:16]=2[O:15][C:14]1=[O:30]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13066716HCID 13066716, compound

Product 1

HCID 13066718HCID 13066718, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of m-chloroperbenzoic acid (1.3 g) in chloroform (20 ml) was added dropwise to a solution of 3-methyl-7-(2-chlorophenylthio)-2,3-dihydrobenzofuran-2-one (1.8 g) in chloroform (20 ml) in 10 minutes at a temperature below 6° C. with stirring, and the mixture was stirred at the same temperature for 30 minutes and then filtered. The organic layer was separated, washed with saturated aqueous sodium bicarbonate and water in turn, dried and evaporated under reduced pressure. The oily residue was crystallized with ethanol to give 3-methyl-7-(2-chlorobenzenesulfinyl)-2,3-dihydrobenzofuran-2-one (1.2 g), mp. 120°-122° C.

Workup

  1. stirringthe mixture was stirred at the same temperature for 30 minutes
  2. filtrationfiltered
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous sodium bicarbonate and water in turn
  5. customdried
  6. customevaporated under reduced pressure
  7. customThe oily residue was crystallized with ethanol

Sources & evidence

ORD record
ord-a119fcd107d34dc7ba45021e174f4f30
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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