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

HRID 724370

반응식

HRID 724370 반응식
[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

참가 물질

5

반응물 2

HCID 24386Thionyl ChlorideHCID 6377974-Chlorocinnamic acid

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 241Benzene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f5deb3535b6b495ca1dba6563ae9bc2e
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141587B2

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