Thionyl Chloride → 3-(4-Chlorophenyl)prop-2-enoyl chloride

HRID 724370

Reaction equation

HRID 724370 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 534112943-(4-Chlorophenyl)prop-2-enoyl 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 (2.51 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, J=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-f5deb3535b6b495ca1dba6563ae9bc2e
Source dataset
uspto-grants-2006_11
Patent number
US07141587B2

Linked notes

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