Sulfuryl chloride → Ethyl 2-chloro-3-oxohexanoate

HRID 1382783Notes

Reaction equation

HRID 1382783 reaction equation
S(Cl)([Cl:4])(=O)=O.[O:6]=[C:7]([CH2:14][CH2:15][CH3:16])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]>C(Cl)(Cl)Cl>[Cl:4][CH:8]([C:7](=[O:6])[CH2:14][CH2:15][CH3:16])[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 238498Ethyl 3-oxohexanoate

Product 1

HCID 11424094Ethyl 2-chloro-3-oxohexanoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Sulphuryl chloride (175 ml) was added to a rapidly stirred and cooled solution of ethyl 3-oxohexanoate (300 ml) in chloroform (150 ml) whilst maintaining the temperature at 10°-15°. The mixture was stirred overnight at room temperature, then heated under reflux for 0.5 h. The cooled reaction mixture was washed with water (0.5 l), 2N sodium bicarbonate (0.5 l) and water (0.5 l), dried and concentrated in vacuo. Fractionation gave the title compound (341.8 g) as a pale yellow liquid b.p. 106°-108°/ca. 10 mmHg, t.l.c. (ether:hexane 1:1), Rf 0.60.

Workup

  1. temperaturewhilst maintaining the temperature at 10°-15°
  2. stirringThe mixture was stirred overnight at room temperature
  3. temperatureheated
  4. temperatureunder reflux for 0.5 h
  5. customThe cooled reaction mixture
  6. washwas washed with water (0.5 l), 2N sodium bicarbonate (0.5 l) and water (0.5 l)
  7. customdried
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-213e9ff9094245ccae36381786429903
Source dataset
uspto-grants-1989_02
Patent number
US04808581

Reaction notes

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