Ethanol → Ethyl (4-chlorophenyl)acetate

HRID 1354998Notes

Reaction equation

HRID 1354998 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[CH2:17]([O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[CH3:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 15880(4-Chlorophenyl)acetic acid

Product 1

HCID 84177Ethyl (4-chlorophenyl)acetateYield 88%

Procedure

A solution of (4-chloro-phenyl)-acetic acid (6.29 g, 0.03 mol) in ethanol (38.4 mL) was treated with a catalytic amount of sulfuric acid. The reaction mixture was heated under reflux for 12 h. The reaction was then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 50/50 hexanes/ethyl acetate) afforded (4-chloro-phenyl)-acetic acid ethyl ester (6.45 g, 88%) as a pale yellow solid: mp 39–41° C.; EI-HRMS m/e calcd for C10H11ClO2 (M+) 198.0448, found 198.0452.

Workup

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

Sources & evidence

ORD record
ord-8b40b5f702d24b0db5f4be03af287a0b
Source dataset
uspto-grants-2007_05
Patent number
US07223868B2

Reaction notes

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