m-Chloroperbenzoic acid → HCID 9817284, compound

HRID 1075467Notes

Reaction equation

HRID 1075467 reaction equation
[CH2:1]([S:8][CH2:9][CH:10]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:11]([OH:13])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:27])C=1>ClCCl>[CH2:1]([S:8]([CH2:9][CH:10]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:11]([OH:13])=[O:12])=[O:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 15410800HCID 15410800, compound

Product 1

HCID 9817284HCID 9817284, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled mixture (-78° C.) of 2-[(benzylsulfanyl)methyl]pentanedioic acid (5.2 g, 19.4 mmol) in dichloromethane (100 ml) was added 3-chloroperbenzoic acid (85%, 3.9 g, 19.4 mmol) with stirring. The reaction mixture was allowed to stir for 1 hour at -78° C., then allowed to warm to room temperature. If starting material was still present according to analysis by TLC, the reaction was cooled again to -78° C. and additional 3-chloroperbenzoic acid (2-4 mmol depending on the intensity of the starting material spot) added and the reaction mixture allowed to warm at room temperature. This was repeated until no more starting material was detected by TLC. The dichloromethane was removed under reduced pressure and the resulting residue was purified by column chromatography to yield 3.8 g (69%) of white solid.

Workup

  1. stirringto stir for 1 hour at -78° C.
  2. temperaturethe reaction was cooled again to -78° C.
  3. additionadded
  4. temperatureto warm at room temperature
  5. customThe dichloromethane was removed under reduced pressure
  6. customthe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-bc69059ad5634987aa4425981ef12ce9
Source dataset
uspto-grants-1999_05
Patent number
US05902817

Reaction notes

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