Water → Ethyl α-chlorobenzeneacetate

HRID 1027968Notes

Reaction equation

HRID 1027968 reaction equation
C(N([CH2:6][CH3:7])CC)C.[Cl:8][CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10](Cl)=[O:11].[OH2:19]>CO>[Cl:8][CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10]([O:19][CH2:6][CH3:7])=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 102902Chloro(phenyl)acetyl chloride

Product 1

HCID 97752Ethyl α-chlorobenzeneacetateYield 83.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of triethylamine (63.5 mmol, 8.7 mL) in methanol there was added dropwise, at 0° C., α-chlorophenylacetyl chloride (53 mmol, 7.6 mL), and the reaction mixture was then stirred over a period of 3.5 h at room temperature. The reaction mixture was then added to 100 mL of water and extracted with EA (3×100 mL). Following the combination of the organic phases, they were dried over MgSO4 and concentrated in vacuo to give 8.76 g (83.4%) of product.

Workup

  1. extractionextracted with EA (3×100 mL)
  2. dry with materialwere dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d062d505fd604c7bad83b6b44a18a10d
Source dataset
uspto-grants-2014_05
Patent number
US08735426B2

Reaction notes

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