Water → HCID 14551712, compound

HRID 265644Notes

Reaction equation

HRID 265644 reaction equation
[C:1]([CH:4]1[CH2:9][CH:8]([CH2:10][CH3:11])[O:7][C:5]1=[O:6])(=[O:3])[CH3:2].S(Cl)([Cl:15])(=O)=O.O>C1C=CC=CC=1>[Cl:15][C:4]1([C:1](=[O:3])[CH3:2])[CH2:9][CH:8]([CH2:10][CH3:11])[O:7][C:5]1=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 24648Sulfuryl chlorideHCID 110518973-Acetyl-5-Ethyldihydro-2(3H)-Furanone

Product 1

HCID 14551712HCID 14551712, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Into a solution of 58.2 g (0.37 moles) of α-acetyl-γ-ethyl-γ-butyrolactone [prepared according to J. Pharm. Sci. 52, 733 (1963)] in 60 cm3 benzene 50 g of (0.37 moles) of sulphuryl chloride are added dropwise under stirring and cooling in 2 hours, keeping the temperature of the reaction mixture between 5 and 10° C. After completing the addition the reaction mixture is let to warm to room temperature and stirred at this temperature until the gas formation ceases. Then it is poured into 400 cm3 of water, the phases are separated and the water is extracted with 200 cm3 of benzene. The benzene containing solution is washed with 100 cm3 of 5% sodium hydrogencarbonate solution. After evaporation the residual oil is distilled in vacuo. The title compound is obtained in the form of a colourless liquid in an amount of 58.9 g (82.5%), its boiling point is 91° C. at a pressure of 80 Pa, nD20 =1,4623.

Workup

  1. temperaturecooling in 2 hours
  2. customthe temperature of the reaction mixture between 5 and 10° C
  3. additionthe addition the reaction mixture
  4. stirringstirred at this temperature until the gas formation ceases
  5. customthe phases are separated
  6. extractionthe water is extracted with 200 cm3 of benzene
  7. washThe benzene containing solution is washed with 100 cm3 of 5% sodium hydrogencarbonate solution
  8. customAfter evaporation the residual oil
  9. distillationis distilled in vacuo

Sources & evidence

ORD record
ord-f104a04c82b94b7fa0b1d74c0029ac95
Source dataset
uspto-grants-1997_07
Patent number
US05648498

Reaction notes

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