4-Nitrophenol → (4'-Nitrophenyl)-4-nitrocinnamate

HRID 380721

反応式

HRID 380721 の反応式
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([CH:8]=[CH:9][C:10](Cl)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+:15]([C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1)([O-:17])=[O:16].N1C=CC=CC=1>CC(C)=O>[N+:15]([C:18]1[CH:23]=[CH:22][C:21]([O:24][C:10](=[O:11])[CH:9]=[CH:8][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:14][CH:13]=2)=[CH:20][CH:19]=1)([O-:17])=[O:16]

参加物

5

反応物 3

HCID 9804-NitrophenolHCID 1049PyridineHCID 3194633-(4-nitrophenyl)prop-2-enoyl Chloride

生成物 1

HCID 53711113(4'-Nitrophenyl)-4-nitrocinnamate収率 95.5%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒2 回

反応条件

温度
50 °C

実験手順

193.2 g (1 mole) of 4-nitrocinnamic acid and 650 g of ethyl acetate were placed in a reaction vessel. While 200 g of thionyl chloride with some drops of DMF was dropped into the reaction mixtures, the reaction mixtures were refluxed with stirring until the generation of hydrogen chloride gas stopped. The reacted solution was concentrated until a solid could be precipitated and was poured into hexane and then the precipitated solid was separated by filtration and dried. 210 g of 4-nitrocinnamoyl chloride was yielded. 64.5 g (0.3 mole) of 4-nitrocinnamoyl chloride and 300 g of acetone were placed in a reaction vessel. The reaction mixtures were heated at 50° C. with stirring under a nitrogen current. 41.73 g (0.3 mole) of 4-nitrophenol, 60 g of pyridine, and 300 g of acetone were added dropwise to the above reaction vessel using a dropping funnel. After the completion of the addition, the reaction mixtures were refluxed with stirring under a nitrogen current for 2 hours. After the reaction, a precipitate was separated by filtration, and the filtrated solid was washed by water and dried. 90 g of light yellow colored needle-like crystals ((4-nitrophenyl)-4-cinnamate)was yielded.

後処理

  1. customThe reaction mixtures
  2. additionAfter the completion of the addition
  3. customthe reaction mixtures
  4. temperaturewere refluxed
  5. stirringwith stirring under a nitrogen current for 2 hours
  6. customAfter the reaction
  7. customa precipitate was separated by filtration
  8. washthe filtrated solid was washed by water
  9. customdried

出典と根拠

ORDレコード
ord-086338c2e6a64c31862edfe61a8af3d1
出典データセット
uspto-grants-2001_10
特許番号
US06303742B1

関連ノート

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