Sulfuryl chloride → Ethyl 2-chloro-3-oxopentanoate

HRID 27489

Reaction equation

HRID 27489 reaction equation
S(Cl)([Cl:4])(=O)=O.[O:6]=[C:7]([CH2:14][CH3:15])[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][CH3:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 78656Ethyl 3-oxovalerate

Product 1

HCID 12923424Ethyl 2-chloro-3-oxopentanoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Sulphuryl chloride (286 g.) was added dropwise to a solution of ethyl 3-oxopentanoate (300 g.) in chloroform (250 ml.) at 10°-15°. Following addition the mixture was stirred overnight at room temperature, heated under reflux for 0.5 hour and cooled. After washing with water, sodium bicarbonate and water, the solution was dried (sodium sulphate), concentrated, and fractionated to yield ethyl 2-chloro-3-oxopentanoate, b.p. 94°-96°/14 mm.

Workup

  1. additionaddition the mixture
  2. temperatureheated
  3. temperatureunder reflux for 0.5 hour
  4. temperaturecooled
  5. washAfter washing with water, sodium bicarbonate and water
  6. dry with materialthe solution was dried (sodium sulphate)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4bf2e9ed074343889166e28dfcebce1b
Source dataset
uspto-grants-1980_09
Patent number
US04221802

Linked notes

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