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

HRID 724370

反応式

HRID 724370 の反応式
[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

参加物

5

反応物 2

HCID 24386Thionyl ChlorideHCID 6377974-Chlorocinnamic acid

生成物 1

HCID 534112943-(4-Chlorophenyl)prop-2-enoyl chloride収率 100.4%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 241Benzene溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f5deb3535b6b495ca1dba6563ae9bc2e
出典データセット
uspto-grants-2006_11
特許番号
US07141587B2

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