m-Chloroperbenzoic acid → Methyl 9,10-epoxyoctadecanoate
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
Product 1
Reagents, catalysts & solvents 1
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.