m-Chloroperbenzoic acid → HCID 12531901, compound

HRID 1863308Notes

Reaction equation

HRID 1863308 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][CH:7]([C:12]2[CH:17]=[CH:16][C:15]([S:18][C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)[C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:36])C=1>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]([C:12]2[CH:17]=[CH:16][C:15]([S:18]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)=[O:36])=[CH:14][CH:13]=2)[C:8]([O:10][CH3:11])=[O:9])=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 12531897HCID 12531897, compound

Product 1

HCID 12531901HCID 12531901, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1,8 g of methyl (p-chlorophenoxy)[p-(p-chlorophenylthio)phenyl]acetate in 10 ml of dichloromethane is added dropwise a solution of 0.891 g of 83% m-chloroperbenzoic acid in 10 ml of dichloromethane. The mixture is chilled overnight, filtered and the filtrate washed with 10% sodium sulfite solution, saturated sodium bicarbonate and sodium chloride solutions. After drying (MgSO4), the solvent is removed under reduced pressure to give a gum. Crystallization from dichloromethane-zepane given 1.65 g of product as white crystals, mp 134°-144° C.

Workup

  1. temperatureThe mixture is chilled overnight
  2. filtrationfiltered
  3. washthe filtrate washed with 10% sodium sulfite solution, saturated sodium bicarbonate and sodium chloride solutions
  4. dry with materialAfter drying (MgSO4)
  5. customthe solvent is removed under reduced pressure
  6. customto give a gum
  7. customCrystallization from dichloromethane-zepane

Sources & evidence

ORD record
ord-f148879ad5b7458caa6c2239bffc9850
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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