Water → Ethyl 2-chloro-3-oxo-3-phenylpropanoate

HRID 896861Notes

Reaction equation

HRID 896861 reaction equation
S(Cl)([Cl:4])(=O)=O.[C:6]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[Cl:4][CH:14]([C:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 7170Ethyl benzoylacetateHCID 24648Sulfuryl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 9855991Ethyl 2-chloro-3-oxo-3-phenylpropanoateYield 84%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of sulfuryl chloride (12.4 mmol) in toluene (5 mL) was added dropwise via an additional funnel to a solution of ethyl benzoylacetate (12.4 mmol) in toluene (20 mL) over 5 minutes at room temperature. The resulting mixture was stirred at room temperature overnight. Water was added slowly and resulting two-phase mixture was basified with saturated NaHCO3 and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, and evaporated to afford 2.2 g (84%) of product as a pale yellow oil; MH+=227.0, retention time (LC-MS)=2.77 min.

Workup

  1. customresulting two-phase mixture
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-a0c5415619484d68ae9ce6085a857e60
Source dataset
uspto-grants-2005_07
Patent number
US06919371B2

Reaction notes

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