Ethanol → Ethyl 3-chloro-4-hydroxyphenylacetate

HRID 984942Notes

Reaction equation

HRID 984942 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-hydroxyphenylacetic acid (10.0 g, 53.0 mmol) in ethanol was dropwise added thionyl chloride (3.9 ml, 53.5 mmol). The mixture was stirred at room temperature for 48 h, concentrated in vacuo and submitted to flash chromatography (graduated from toluene to 5% ethyl acetate in toluene eluent) to give 11.0 g of 3-chloro-4-hydroxyphenylacetic acid ethyl ester.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-61bdef09ffd9418aae0c4fab4f8ec2ad
Source dataset
uspto-grants-2005_03
Patent number
US06869967B2

Reaction notes

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