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

HRID 394967노트

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HRID 394967 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

HCID 1813233,4-Dimethoxy-4'-hydroxychalcone수율 29.3%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 962Water용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c0e2be88bbcd48b4817251b3f4df7315
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06603046B1

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