m-Chloroperbenzoic acid → 2500-59-6

HRID 2279684Notes

Reaction equation

HRID 2279684 reaction equation
[C:1]([O:20][CH3:21])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].ClC1C=CC=C(C(OO)=[O:30])C=1>ClCCl>[CH2:11]([CH:10]1[O:30][CH:9]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([O:20][CH3:21])=[O:19])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 5364509Methyl Oleate

Product 1

HCID 5439232500-59-6

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl oleate (1) (5.0 g; 0.017 mol) (89%) (ITERG) and meta-chloroperbenzoic acid (mCPBA) (4.3 g; 0.025 mol) (Aldrich) were dissolved in dichloromethane (J. T. Baker) (100 mL) and the reaction mixture was mixed under agitation at ambient temperature for 5 hours. The reaction mixture was then filtered and the collected solution was washed with saturated aqueous sodium bicarbonate (3×50 mL) (Aldrich) then with water (3×50 mL). The organic layer was separated and dried over anhydrous sodium sulfate. Finally, the solvent was removed by evaporation under rotation to obtain the intermediate compound 2.

Workup

  1. additionthe reaction mixture was mixed under agitation at ambient temperature for 5 hours
  2. filtrationThe reaction mixture was then filtered
  3. washthe collected solution was washed with saturated aqueous sodium bicarbonate (3×50 mL) (Aldrich)
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. customFinally, the solvent was removed by evaporation under rotation

Sources & evidence

ORD record
ord-e535bc0e18e74cdbaa96dd3b6bc4c323
Source dataset
uspto-grants-2015_09
Patent number
US09133305B2

Reaction notes

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