m-Chloroperbenzoic acid → HCID 86734833, compound

HRID 436872Notes

Reaction equation

ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]([CH3:31])([C:18](=[O:30])[CH2:19][CH2:20][CH:21]=[C:22]([CH3:29])[CH2:23][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])[C:14]([O:16][CH3:17])=[O:15].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[O:9]1[C:26]([CH3:28])([CH3:27])[CH:25]1[CH2:24][CH2:23][C:22]([CH3:29])=[CH:21][CH2:20][CH2:19][C:18](=[O:30])[C:13]([CH3:31])([CH3:12])[C:14]([O:16][CH3:17])=[O:15]

Participants

Conditions

Temperature: -50 °C

Procedure

A solution of 1.32 g of m-chloroperbenzoic acid in 50 ml of methylene chloride was added to a solution of 1.93 g of the product of Step A in 50 ml of methylene chloride cooled to -50° C. and the mixture was stirred for 1 hour at -40° C. and 21/2 hours at -5° C. The mixture was poured into a saturated aqueous sodium bicarbonate solution and the organic phase was decanted. The aqueous phase was extracted with methylene chloride and the combined organic phases were washed with water, dried over sodium sulfate and evaporated to dryness. The residue was chromatographed over silica and was eluted with a 95-5 mixture of benzene and ethyl acetate to obtain 0.88 g of methyl 10-epoxy-2,2,7,11-tetramethyl-3-oxo-6-dodecenoate in the form of a colorless oil.

Workup

custom2 hours
customat -5° C
customthe organic phase was decanted
extractionThe aqueous phase was extracted with methylene chloride
washthe combined organic phases were washed with water
dry with materialdried over sodium sulfate
customevaporated to dryness
customThe residue was chromatographed over silica
washwas eluted with a 95-5 mixture of benzene and ethyl acetate

Sources & evidence

ORD record: ord-732358b82ffd45bba5819e84932e7dc6
Source dataset: uspto-grants-1977_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04028386

Reaction notes

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