Vanillin → 1-(4'-Hydroxy,3'-methoxyphenyl)-4-phenyl-1-butene-3-one

HRID 847538노트

반응식

HRID 847538 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[O:10][CH3:11].C1([PH2]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)C2C=CC=CC=2)C=CC=CC=1.[O:31](CC(=O)C)[C:32]1[CH:37]=CC=C[CH:33]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:33][C:32](=[O:31])[CH2:37][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:4][C:3]=1[O:10][CH3:11]

참가 물질

5

반응물 2

HCID 1183VanillinHCID 178468789HCID 178468789, 화합물

생성물 1

HCID 539208741-(4'-Hydroxy,3'-methoxyphenyl)-4-phenyl-1-butene-3-one수율 81%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

4-Hydroxy-3-methoxybenzaldehyde (2.1 g, 13.8 mMol) and 3-phenoxypropane-2-one triphenylphosphorane (2.8 g, 6.9 mMol) (prepared as described by LeCorre: C. R. Acad. Sci. Paris 273 81 (1971)) are dissolved in 100 ml of toluene and warmed to reflux. After three hours, the solvent is evaporated and the residue is taken up in tHF. Sodium bisulfite (10.0 g) is dissolved in 100 ml of water and stirred with the solution for one hour. The THF is evaporated and the water is extracted with chloroform. Drying over magnesium sulfate and evaporation of the chloroform gives a yellow oil. Flash chromatography in ethyl acetate on silica gel gives 1.5 g (65%) of 1-(4'-hydroxy,3'-methoxyphenyl)-4-phenyl-1-butene-3-one; mp=85°-87° C. C, H analysis: Calcd for C17H16O4 (71.81, 5.68); Found (71.85, 5.50).

후처리

  1. temperaturewarmed to reflux
  2. customthe solvent is evaporated
  3. dissolutionSodium bisulfite (10.0 g) is dissolved in 100 ml of water
  4. customThe THF is evaporated
  5. extractionthe water is extracted with chloroform
  6. dry with materialDrying over magnesium sulfate and evaporation of the chloroform
  7. customgives a yellow oil

출처 및 근거

ORD 기록
ord-76a03d7971514bcdbf854d0267151164
출처 데이터셋
uspto-grants-1992_08
특허 번호
US05142095

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