p-Toluenesulfonic acid → 3,4-Dimethoxy-4'-hydroxychalcone

HRID 394967ノート

反応式

HRID 394967 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21]CC=C)=[CH:17][CH:16]=2)=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.O.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]([C:15]2[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=2)=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

参加物

6

反応物 2

HCID 6101p-Toluenesulfonic acidHCID 544817843,4-Dimethoxy-4'-allyloxychalcone

生成物 1

HCID 1813233,4-Dimethoxy-4'-hydroxychalcone収率 29.3%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

486 mg (1.5 mmol) of 3,4-dimethoxy-4′-allyloxychalcone was dissolved in a mixture of 7.5 ml of methanol and 1.5 ml of water. To the solution were added 150 mg of p-tolu-enesulfonic acid and 150 mg of palladium on carbon (10%) and the solution was heated to 80° C. for 2 h in a sealed flask. The reaction mixture was filtered and poured into a mixture of 10 ml of an aqueous 10% solution of sodium bicarbonate and 10 ml of a saturated aqueous solution of sodium chloride. The mixture was extracted with 15 ml of ethyl acetate and concentrated in vacuo. The residue was recrystallized from methanol to give 0.125 g (25%) of 3,4-dimethoxy-4′-hydroxychalcone (m.p. 193-198° C.) identical to that described by A.v.n Wacek, and E. David, Ber. 70 (1937), 190 (m.p. 208° C.

後処理

  1. filtrationThe reaction mixture was filtered
  2. additionpoured into a mixture of 10 ml of an aqueous 10% solution of sodium bicarbonate and 10 ml of a saturated aqueous solution of sodium chloride
  3. extractionThe mixture was extracted with 15 ml of ethyl acetate
  4. concentrationconcentrated in vacuo
  5. customThe residue was recrystallized from methanol

出典と根拠

ORDレコード
ord-c0e2be88bbcd48b4817251b3f4df7315
出典データセット
uspto-grants-2003_08
特許番号
US06603046B1

反応ノート

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