Water → HCID 15374214, compound

HRID 1081956Notes

Reaction equation

HRID 1081956 reaction equation
C1C=C([O:7]O)C(C(O)=O)=C(C(O)=O)C=1.[C:15]([O:23][CH2:24][CH:25]1[S:29][CH2:28][CH2:27][O:26]1)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[C:15]([O:23][CH2:24][CH:25]1[S:29](=[O:7])[CH2:28][CH2:27][O:26]1)(=[O:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 962WaterHCID 110640761,3-Oxathiolane-2-methanol, 2-benzoateHCID 198097063-Hydroperoxyphthalic acid

Product 1

HCID 15374214HCID 15374214, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

Monoperoxyphthalic acid, magnesium salt (MMPP, 28 g) was added portionwise under vigorous stirring to a mixture of 2-benzoyloxymethyl-1,3-oxathiolane (example 2) (20 g), tetrabutyl ammonium bromide (0.4 g) in methylene chloride (200 ml), and water (200 ml). The mixture was stirred at room temperature for 30 minutes and the organic layer was collected. The aqueous phase was extracted with methylene chloride (3×75 ml) and the combined organic layer was washed first with water (2×100 ml), then with brine solution (100 ml), dried over MgSO4, and filtered. The filtrate was evaporated in vacuo and the residue was purified by chromatography on silica gel using ethyl acetate as eluant to give 18.5 g (86%) of pure product as a mixture of cis- and trans- isomers in a ratio of 1:2 respectively.

Workup

  1. customthe organic layer was collected
  2. extractionThe aqueous phase was extracted with methylene chloride (3×75 ml)
  3. washthe combined organic layer was washed first with water (2×100 ml)
  4. dry with materialwith brine solution (100 ml), dried over MgSO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated in vacuo
  7. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-45fab0c8ba7545b9a776a173436a05d5
Source dataset
uspto-grants-1996_12
Patent number
US05587480

Reaction notes

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