Carbon Tetrachloride → Ethyl 2-chloro-3-oxo-3-phenylpropanoate

HRID 1439349Notes

Reaction equation

HRID 1439349 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].C([O-])(=O)C.[Na+].C(Cl)(Cl)(Cl)[Cl:21].S(Cl)(Cl)(=O)=O>C(O)(=O)C.C(OCC)(=O)C.O>[CH2:1]([O:3][C:4](=[O:14])[CH:5]([C:6](=[O:13])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[Cl:21])[CH3:2]

Participants

8

Reactant 4

HCID 5943Carbon TetrachlorideHCID 7170Ethyl benzoylacetateHCID 24648Sulfuryl chlorideHCID 517045Sodium Acetate

Product 1

HCID 9855991Ethyl 2-chloro-3-oxo-3-phenylpropanoate

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

119.5 g of benzoyl acetic acid ethyl ester and 53.4 g of sodium acetate sicc. were dissolved in 1 l of glacial acetic acid and 100 ml of carbon tetrachloride at 40° C. A solution of 52 ml of sulphuryl chloride (density 1.67) in 50 ml of glacial acetic acid was added dropwise with vigorous stirring at 35°-40° C over a period of one hour. The reaction mixture was then stirred for one hour at 40° C and poured on about 10 l of water. The precipitated oily product was taken up with ethyl acetate and treated in the usual manner. 124 g of α-chlorobenzoylacetic acid ethyl ester were obtained.

Workup

  1. customat 40° C
  2. stirringThe reaction mixture was then stirred for one hour at 40° C
  3. additiontreated in the usual manner

Sources & evidence

ORD record
ord-6ab83a25b5984687b700ab27f15ebde5
Source dataset
uspto-grants-1977_11
Patent number
US04059447

Reaction notes

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