Ethanol → Ethyl 4-hydroxyhydrocinnamate

HRID 984938Notes

Reaction equation

HRID 984938 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH2:17](O)[CH3:18]>>[CH2:17]([O:11][C:10](=[O:12])[CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)[CH3:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 103943-(4-Hydroxyphenyl)propionic acidHCID 24386Thionyl Chloride

Product 1

HCID 2736435Ethyl 4-hydroxyhydrocinnamateYield 99%

Procedure

To an ice-cooled solution of 3-(p-hydroxyphenyl)-propionic acid (8.3 g, 50.0 mmol) in ethanol (100 mL) was dropwise added thionyl chloride (3.7 mL, 50.7 mmol). The mixture was stirred at room temperature over night, concentrated in vacuo and the residue purified by kugelrohr distillation, to give 9.6 g (99%) of 3-(4-hydroxy-phenyl)-propionic acid ethyl ester as a colourless oil.

Workup

  1. concentrationconcentrated in vacuo
  2. distillationthe residue purified by kugelrohr distillation

Sources & evidence

ORD record
ord-b0eb1d2d77a64f1ca90c61164bb091c7
Source dataset
uspto-grants-2005_03
Patent number
US06869967B2

Reaction notes

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