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Methyl Acrylate → 4-(m-Methylcinnamyl)-4-phenyl-5-oxo-7-(p-chlorophenyl)-6-heptenoic Acid

HRID 1076327
ノート
印刷プレビュー

反応式

HRID 1076327 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10](=[O:28])[CH:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:12][CH:13]=[CH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=2)=[CH:4][CH:3]=1.[C:29]([O:33]C)(=[O:32])[CH:30]=[CH2:31]>CO.C(COC)OC>[CH3:21][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[CH:14]=[CH:13][CH2:12][C:11]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:10](=[O:28])[CH:9]=[CH:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH2:31][CH2:30][C:29]([OH:33])=[O:32]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 7294Methyl AcrylateHCID 541666091-(p-Chlorophenyl)-4-phenyl-7-(m-methylphenyl)-1,6-heptadien-3-one

生成物 1

HCID 540475534-(m-Methylcinnamyl)-4-phenyl-5-oxo-7-(p-chlorophenyl)-6-heptenoic Acid

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 80711,2-Dimethoxyethane溶媒2 回

実験手順

Triton B (2 ml., 40% in MeOH) is added to a stirred solution of 1-(p-chlorophenyl)-4-phenyl-7-(m-methylphenyl)-1,6-heptadien-3-one (19.33 g., 0.05 mole) in glyme (250 ml.) followed by the addition of methyl acrylate (4.73 g., 0.055 mole) in glyme (50 ml.). The solution is stirred for 96 hours and the solvent is removed under reduced pressure. The residue is suspended in methanol (700 ml.) and a 20% sodium hydroxide solution (35 ml.) is added. After an additional 24 hours, the methanol is evaporated in vacuo and the residue is dissolved in water. Extraction with ether removes unreacted ketone. The aqueous solution is acidified and the solid that separates is collected, washed well with water, and air-dried, yield 9.78 g., m.p. 135°-144°C. Recyrstallization from butyl chloride produces material with m.p. 154°-155°C.

後処理

  1. customthe solvent is removed under reduced pressure
  2. additiona 20% sodium hydroxide solution (35 ml.) is added
  3. waitAfter an additional 24 hours
  4. customthe methanol is evaporated in vacuo
  5. dissolutionthe residue is dissolved in water
  6. extractionExtraction with ether
  7. customremoves unreacted ketone
  8. customthe solid that separates is collected
  9. washwashed well with water
  10. customair-dried
  11. customRecyrstallization from butyl chloride produces material with m.p. 154°-155°C.

出典と根拠

ORDレコード
ord-29090e2d2fda4bf58e119ef5fd19eff9
出典データセット
uspto-grants-1976_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US03956374

反応ノート

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