3-(3'-Hydroxyphenyl)propionic acid → Ethyl 3-(3-hydroxyphenyl)propanoate

HRID 984936Notes

Reaction equation

HRID 984936 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][CH:7]=1.S(Cl)(Cl)=O.[CH2:17](O)[CH3:18]>>[CH2:17]([O:11][C:10](=[O:12])[CH2:9][CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=1)[CH3:18]

Participants

4

Reactant 3

HCID 913-(3'-Hydroxyphenyl)propionic acidHCID 702EthanolHCID 24386Thionyl Chloride

Product 1

HCID 15197885Ethyl 3-(3-hydroxyphenyl)propanoate

Procedure

To an ice-cooled solution of 3-(3-hydroxyphenyl)propionic acid (20.0 g, 120 mmol) in ethanol was dropwise added thionyl chloride (8.8 ml, 120 mmol). The mixture was stirred at room temperature over night, concentrated in vacuo and submitted to flash chromatography (10% ethyl acetate in toluene eluent) to give 23.3 g of 3-(3-hydroxy-phenyl)propionic acid ethyl ester.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c7fea8ab776543e3970a771c2c555a01
Source dataset
uspto-grants-2005_03
Patent number
US06869967B2

Reaction notes

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