m-Chloroperbenzoic acid → HCID 545978, compound

HRID 1608020Notes

Reaction equation

HRID 1608020 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1([CH3:20])[CH:18]=[CH:17][O:16][C:15](=[O:19])[CH2:14]1>>[O:9]1[CH:17]2[CH:18]1[C:13]([CH3:20])([CH3:12])[CH2:14][C:15](=[O:19])[O:16]2

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 30186853,4-Dihydro-4,4-dimethyl-2H-pyran-2-one

Product 1

HCID 545978HCID 545978, compoundYield 81.3%

Procedure

A solution of 43.15 g of m-chloroperbenzoic acid in 25.2 g of 4,4-dimethyl-3,4-dihydro-2-pyrone at 0° C. was stirred for 3 hours while allowing the temperature to rise to room temperature and was then vacuum filtered. The product was empasted with methylene chloride and the filtrate was washed with an aqueous sodium thiosulfate, then with water. The organic phase was dried and evaporated to dryness under reduced pressure to obtain 28.5 g of raw product which was chromatographed over silica gel and eluted with an hexane-isopropyl ether to obtain 23.08 g of racemic 5,6-epoxy-4,4-dimethyl-tetrahydro-pyr-2-one melting towards 22° C.

Workup

  1. customto rise to room temperature
  2. filtrationvacuum filtered
  3. washthe filtrate was washed with an aqueous sodium thiosulfate
  4. customThe organic phase was dried
  5. customevaporated to dryness under reduced pressure
  6. customto obtain 28.5 g of raw product which
  7. customwas chromatographed over silica gel
  8. washeluted with an hexane-isopropyl ether

Sources & evidence

ORD record
ord-071520b30023466e942d479bbf63ba23
Source dataset
uspto-grants-1989_09
Patent number
US04868317

Reaction notes

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