Santonox → HCID 86589160, compound

HRID 2305012Notes

Reaction equation

HRID 2305012 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH2:12][C:13](=[CH2:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1.S(C1C=C(C(C)(C)C)C(O)=CC=1C)C1C=C(C(C)(C)C)C([OH:31])=CC=1C.ClC1C=C(C=CC=1)C(OO)=O>C(Cl)CCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH2:12][C:13]2([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:19][O:31]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7308SantonoxHCID 70297m-Chloroperbenzoic acidHCID 86589161HCID 86589161, compound

Product 1

HCID 86589160HCID 86589160, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To 2[(4-methoxybenzenesulfonyl)methyl]-acrylic acid, ethyl ester (38.4 g, 0.152 mol) in 200 mL of ethylene dichloride is added a small amount of the radical inhibitor 4,4′-thiobis-(6-t-butyl-3-methylphenol) [Ref: J.C.S. Chem. Commun., 1972, pp 64-65]. Technical grade m-chloroperoxybenzoic acid (MCPBA, 154 g) is added portionwise over about 45 minutes. The reaction becomes a heavy white slurry. Additional ethylene dichloride (150 mL) is introduced to facilitate stirring. The reaction is refluxed overnight, then cooled and concentrated under reduced pressure. The residue is mixed with ethyl acetate (250 mL) and aqueous sodium sulfite. Solid potassium bicarbonate is then slowly added. The phases are separated , and the aqueous phase is extracted with additional ethyl acetate (100 mL). The combined organic phases are washed with several portions of aqueous potassium bicarbonate, then saturated brine, and finally dried over magnesium sulfate. Filtration and evaporation provides the crude product as a pale yellow oil. Chromatography on silica gel, eluting with a gradient of 40% to 60% ethyl acetate in hexanes, affords the title compound. m.p. 77-79° C.;

Workup

  1. temperatureThe reaction is refluxed overnight
  2. temperaturecooled
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue is mixed with ethyl acetate (250 mL) and aqueous sodium sulfite
  5. additionSolid potassium bicarbonate is then slowly added
  6. customThe phases are separated
  7. extractionthe aqueous phase is extracted with additional ethyl acetate (100 mL)
  8. washThe combined organic phases are washed with several portions of aqueous potassium bicarbonate
  9. dry with materialsaturated brine, and finally dried over magnesium sulfate
  10. filtrationFiltration and evaporation
  11. customprovides the crude product as a pale yellow oil
  12. washChromatography on silica gel, eluting with a gradient of 40% to 60% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-17a8c385afa04f598c183e04b61d1540
Source dataset
uspto-grants-2002_08
Patent number
US06437177B1

Reaction notes

Loading…