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

HRID 621228Notes

Reaction equation

HRID 621228 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, fthe 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. extractionfthe 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-fe7a86403f414139a41ca0f9c7d23199
Source dataset
uspto-grants-1989_04
Patent number
US04822888

Reaction notes

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