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

HRID 1076327
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인쇄 미리보기

반응식

HRID 1076327 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 80711,2-Dimethoxyethane용매2회

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-29090e2d2fda4bf58e119ef5fd19eff9
출처 데이터셋
uspto-grants-1976_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US03956374

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