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

HRID 1032859ノート

反応式

HRID 1032859 の反応式
[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](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:31]([CH2:38][C:39](=[O:41])[CH3:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][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:40][C:39](=[O:41])[CH2:38][O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:4][C:3]=1[O:10][CH3:11]

参加物

5

反応物 2

HCID 1183VanillinHCID 178468789HCID 178468789、化合物

生成物 1

HCID 538589221-(4'-Hydroxy,3'-methoxyphenyl)-4-phenoxy-1-butene-3-one収率 76.5%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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-phenoxy-1-butene-3-one; mp=85°-87° C. C, H analysis Calcd for C17H16O4 (71.81, 5.68); Found (71.85, 5.50).

後処理

  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

出典と根拠

ORDレコード
ord-5356df36477b4f1989f774563696b752
出典データセット
uspto-grants-1990_09
特許番号
US04959503

反応ノート

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