Ethanol → Ethyl 3-chloro-4-hydroxyphenylacetate

HRID 984950Notes

Reaction equation

HRID 984950 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].S(Cl)(Cl)=O.[CH2:17](O)[CH3:18]>>[CH2:17]([O:11][C:10](=[O:12])[CH2:9][C:4]1[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([Cl:1])[CH:3]=1)[CH3:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 1185343-Chloro-4-hydroxyphenylacetic acid

Product 1

HCID 11031224Ethyl 3-chloro-4-hydroxyphenylacetate

Procedure

To an ice-cooled solution of 3-chloro-4-hydroxyphenyl-acetic acid (10.0 g, 53 mmol) in ethanol was dropwise added thionyl chloride (3.9 mL. 53.5 mmol). The mixture was stirred at room temperature over night, concentrated in vacuo and submitted to flash chromatography (eluent: graduated from 10% ethyl acetate in toluene to toluen) to give 11 g of 3-chloro-4-hydroxyphenyl-acetic acid ethyl ester.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e2c860c191e544f3b7fccf9ceb0f6f2c
Source dataset
uspto-grants-2005_03
Patent number
US06869967B2

Reaction notes

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