m-Chloroperbenzoic acid → HCID 86734834, compound

HRID 436874Notes

Reaction equation

ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]([CH2:25][CH2:26][CH:27]=[C:28]([CH3:30])[CH3:29])=[CH:14][CH2:15][CH2:16][C:17](=[O:24])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[O:9]1[C:28]([CH3:29])([CH3:30])[CH:27]1[CH2:26][CH2:25][C:13]([CH3:12])=[CH:14][CH2:15][CH2:16][C:17](=[O:24])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

Conditions

Temperature: -50 °C

Procedure

A solution of 2.59 g of m-chloroperbenzoic acid in 50 ml of methylene chloride was added to a solution of 3.6 g of the product of Step A in 50 ml of methylene chloride cooled to -50° C. and the mixture was held at -5° C. for 1 hour and was then poured into a saturated aqueous sodium bicarbonate solution. The organic phase was decanted and the aqueous phase was extracted with methylene chloride. The organic extracts were washed with water, dried over sodium sulfate and evaporated to dryness. The residue was chromatographed over silica and was eluted with a 7-3 benzene-ethyl acetate mixture to obtain 2.2 g of ethyl 10-epoxy-7,11-dimethyl-3-oxo- 6-dodecenoate in the form of a pale yellow oil with a refractive index of nD22 = 1.4662.

Workup

customThe organic phase was decanted
extractionthe aqueous phase was extracted with methylene chloride
washThe organic extracts were washed with water
dry with materialdried over sodium sulfate
customevaporated to dryness
customThe residue was chromatographed over silica
washwas eluted with a 7-3 benzene-ethyl acetate mixture

Sources & evidence

ORD record: ord-89d7109d225f4ba592e8f7cf568f61bc
Source dataset: uspto-grants-1977_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04028386

Reaction notes

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