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

HRID 1816794

Reaktionsgleichung

Reaktionsgleichung von HRID 1816794
[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

Komponenten

5

Edukt 2

HCID 24386Thionyl ChlorideHCID 6377974-Chlorocinnamic acid

Produkt 1

HCID 534112943-(4-Chlorophenyl)prop-2-enoyl chlorideAusbeute 100,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 241BenzeneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-bcb4e4038c8d4deb85065412d76a4aed
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06884890B2

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