Thionyl Chloride → 4-Chlorocinnamoyl chloride

HRID 1816794Notes

Reaction equation

HRID 1816794 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5](/[CH:6]=[CH:7]/[C:8](O)=[O:9])=[CH:4][CH:3]=1.S(Cl)([Cl:15])=O>C1C=CC=CC=1.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([Cl:15])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 6377974-Chlorocinnamic acid

Product 1

HCID 534112944-Chlorocinnamoyl chlorideYield 100.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 241BenzeneSolvent

Procedure

3-(4-chloro-phenyl)-acryloyl chloride was prepared as follows: To a stirred suspension of 4-chloro-trans-cinnamic acid (251 g, 13.77 mmol) in benzene was added thionyl chloride (1.1 mL, 15.14 mmol) and a catalytic amount of DMAP. The reaction mixture was heated at reflux for 1.5 h. The volatile materials were removed under reduced pressure. The white residue was dissolved in Et2O and concentrated again under reduced pressure, to give 3-(4-chloro-phenyl)-acryloyl chloride (2.78 g, quantitative) as a white solid: 1H NMR (CDCl3) δ 7.81 (d, 1H, 1=15.6 Hz), 7.54 (d, 2H, J=8.6 Hz), 7.44 (d, 2H, J=8.6 Hz), 6.65 (d, 1H, J=15.6 Hz).

Workup

  1. custom3-(4-chloro-phenyl)-acryloyl chloride was prepared
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 1.5 h
  4. customThe volatile materials were removed under reduced pressure
  5. dissolutionThe white residue was dissolved in Et2O
  6. concentrationconcentrated again under reduced pressure

Sources & evidence

ORD record
ord-bcb4e4038c8d4deb85065412d76a4aed
Source dataset
uspto-grants-2005_04
Patent number
US06884890B2

Reaction notes

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