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

HRID 1836957Notes

Reaction equation

HRID 1836957 reaction equation
S(Cl)([Cl:4])(=O)=O.[C:6]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(=[O:10])[CH:7]([CH3:9])[CH3:8].O.C([O-])(O)=O.[Na+].[C:23]1([CH3:29])C=CC=C[CH:24]=1>>[Cl:4][CH:11]([C:6](=[O:10])[C:7]1[CH:9]=[CH:29][CH:23]=[CH:24][CH:8]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 5

HCID 962WaterHCID 1140Toluene2×HCID 24648Sulfuryl chlorideHCID 81583Ethyl isobutyrylacetateHCID 516892Sodium Bicarbonate

Product 1

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

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 isobutyrylacetate (12.4 mmol) in toluene (20 mL) over 5 minutes at rt. The resulting mixture was stirred at rt overnight. Water was added slowly. The resulting two-phase mixture was basified with saturated NaHCO3 and extracted with EtOAc. The combined organic extracts were washed with brine, dried over anhyd. sodium sulfate, and removed in vacuo 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. extractionextracted with EtOAc
  2. washThe combined organic extracts were washed with brine
  3. customdried over anhyd
  4. customsodium sulfate, and removed in vacuo

Sources & evidence

ORD record
ord-8d2d2b7c85524030b7c8c8a72a1d8240
Source dataset
uspto-grants-2004_08
Patent number
US06780859B2

Reaction notes

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