m-Chloroperbenzoic acid → HCID 20034837, compound

HRID 231257Notes

Reaction equation

HRID 231257 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][S:5][CH2:6][CH2:7][CH:8]([O:29][CH3:30])[CH2:9][O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].ClC1C=CC=C(C(OO)=[O:39])C=1>ClCCl>[CH3:30][O:29][CH:8]([CH2:9][O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:7][CH2:6][S:5]([CH2:4][CH2:3][CH2:2][OH:1])=[O:39]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 54387312HCID 54387312, compound

Product 1

HCID 20034837HCID 20034837, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 20 ml of dichloromethane is dissolved 1.52 g of 3-methoxy-4-octadecyloxybutyl 3-hydroxypropyl sulfide, to which a solution of 0.61 g of m-chloroperbenzoic acid in 8 ml of dichloromethane is added dropwise with stirring under ice cooling. Thereafter, the mixture is stirred at room temperature for 30 minutes to complete the reaction. The reaction mixture is then washed with an aqueous sodium bisulfite solution, an aqueous sodium bicarbonate solution and then water and dried. The solvent is distilled off under reduced pressure and the residue is purified by silica gel column chromatography to obtain 1.46 g of the captioned compound.

Workup

  1. stirringThereafter, the mixture is stirred at room temperature for 30 minutes
  2. customthe reaction
  3. washThe reaction mixture is then washed with an aqueous sodium bisulfite solution
  4. dry with materialan aqueous sodium bicarbonate solution and then water and dried
  5. distillationThe solvent is distilled off under reduced pressure
  6. customthe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5163813343e44776bfe7b20d7e8c32b0
Source dataset
uspto-grants-1989_07
Patent number
US04845219

Reaction notes

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