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

HRID 1193510ノート

反応式

HRID 1193510 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 3 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-c1d3a6745e0d46009c164950fdb23ba7
出典データセット
uspto-grants-1989_03
特許番号
US04810716

反応ノート

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