Performic Acid → 9,10-Epoxystearic acid

HRID 1527835Notes

Reaction equation

[C:1]([OH:20])(=[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].C(OO)=[O:22]>>[O:22]1[CH:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:9]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:20])=[O:19]

Participants

Reactant 2

HCID 66051Performic Acid

HCID 445639Oleic Acid

Product 1

HCID 158689,10-Epoxystearic acid

Procedure

9,10-Epoxyoctadecanoic acid is prepared according to a method described in “Salimon et al., (2009), European Journal of Scientific Research, 32(2), 216-222” and in which 71 mmol of oleic acid are treated with freshly prepared performic acid at ambient temperature for 3 hours with magnetic stirring (400 rpm). A white powder of 9,10-epoxyoctadecanoic acid (51 mmol) is obtained, with a degree of purity of 65% and a yield of 72%.

Workup

custom9,10-Epoxyoctadecanoic acid is prepared

Sources & evidence

ORD record: ord-04e1c826161f47d18d61d30cb88db6ca
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090552B2

Reaction notes

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