m-Chloroperbenzoic acid → HCID 14989149, compound

HRID 359735Notes

Reaction equation

HRID 359735 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([S:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].ClC1C=C(C=CC=1)C(OO)=[O:28]>ClCCl>[CH3:15][C:12]([C:9]1[CH:8]=[C:7]([S:16]([CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[O:28])[CH:6]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[C:10]=1[OH:11])([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13531084HCID 13531084, compound

Product 1

HCID 14989149HCID 14989149, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]propanoate (0.5 g, 1.5 mmole) and meta-chloroperoxybenzoic acid (0.32 g, 1.5 mmole) in dichloromethane (25 ml) was stirred under argon for 12 hours. Excess peroxide was destroyed with saturated aqueous potassium bisulfite and the phases were separated. The organic layer was washed with water, dried over magnesium sulfate, filtered, and concentrated in vacuo to dryness Recrystallization from diethyl ether and dichloromethane gave the title compound m.p. 106°-108°.

Workup

  1. customExcess peroxide was destroyed with saturated aqueous potassium bisulfite
  2. customthe phases were separated
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to dryness Recrystallization from diethyl ether and dichloromethane

Sources & evidence

ORD record
ord-04895b5cf0414757800cd8357d9b39da
Source dataset
uspto-grants-1991_03
Patent number
US05002967

Reaction notes

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