Ethanol → Ethyl 2-(3-chlorophenyl)acetate

HRID 966558Notes

Reaction equation

HRID 966558 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[CH2:17]([O:10][C:9](=[O:11])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH3:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 158793-Chlorophenylacetic acid

Product 1

HCID 8063366Ethyl 2-(3-chlorophenyl)acetateYield 86.8%

Procedure

(3-Chloro-phenyl)-acetic acid (6.03 g, 0.03 mol) was dissolved in ethanol (37.7 mL) and treated with a catalytic amount of sulfuric acid. The reaction mixture was heated under reflux for 12 h. The reaction was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50/50 hexanes/ethyl acetate) afforded (3-chloro-phenyl)-acetic acid ethyl ester (6.10 g, 86.8%) as a clear oil: EI-HRMS m/e calcd for C10H11ClO2(M+) 198.0448, found 198.0442.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 12 h
  3. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-67b890cb18434d1d8c1ee692c01e49b5
Source dataset
uspto-grants-2005_10
Patent number
US06951945B2

Reaction notes

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