Acetic Acid → Ethyl 2-(butoxyimino)-4-chloro-3-oxobutanoate

HRID 364467Notes

Reaction equation

HRID 364467 reaction equation
[CH2:1]([O:5][N:6]=[C:7]([C:13](=[O:15])[CH3:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:2][CH2:3][CH3:4].S(Cl)([Cl:19])(=O)=O.C(O)(=O)C>O>[CH2:1]([O:5][N:6]=[C:7]([C:13](=[O:15])[CH2:14][Cl:19])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24648Sulfuryl chlorideHCID 53974956Ethyl 2-(butoxyimino)-3-oxobutanoate

Product 1

HCID 54055311Ethyl 2-(butoxyimino)-4-chloro-3-oxobutanoateYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of ethyl 2-n-butoxyimino-3-oxobutyrate (syn isomer, 48.8 g.), sulfuryl chloride (31.5 g.) and acetic acid (48.8 ml.) was stirred at 40° C. for 10 minutes and further at room temperature for 5.5 hours. After water (300 ml.) was added to the resultant solution under ice cooling, the solution was extracted with methylene chloride three times. The extract was washed with water, an aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride in turn, and dried over magnesium sulfate. The solution was concentrated in vacuo to give ethyl 2-n-butoxyimino-4-chloro-3-oxobutyrate (syn isomer, 52.1 g.), oil.

Workup

  1. extractionthe solution was extracted with methylene chloride three times
  2. washThe extract was washed with water
  3. dry with materialan aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride in turn, and dried over magnesium sulfate
  4. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-a22a2f165c8e409f8328f1a3118c8876
Source dataset
uspto-grants-1986_08
Patent number
US04604456

Reaction notes

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