2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 6-Hydroxy-7-methoxy-5-benzofurancarboxaldehyde

HRID 26374

반응식

HRID 26374 반응식
C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.[OH:15][C:16]1[C:24]([CH:25]=[O:26])=[CH:23][C:19]2[CH2:20][CH2:21][O:22][C:18]=2[C:17]=1[O:27][CH3:28]>O1CCOCC1>[OH:15][C:16]1[C:24]([CH:25]=[O:26])=[CH:23][C:19]2[CH:20]=[CH:21][O:22][C:18]=2[C:17]=1[O:27][CH3:28]

참가 물질

4

반응물 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 218565722,3-Dihydro-6-hydroxy-7-methoxy-5-benzofurancarboxaldehyde

생성물 1

HCID 217856846-Hydroxy-7-methoxy-5-benzofurancarboxaldehyde

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

실험 절차

A solution of 817 mg. (3.6 mmole) of DDQ in 10 ml. of dioxane was added to 582 mg. (3 mmole) of 2,3-dihydro-6-hydroxy-7-methoxy-5-benzofuran-carboxaldehyde in 15 ml. of dioxane and the resulting mixture was heated under reflux for 7 hours, cooled and the formed solid removed by filtration. The precipitate was thoroughly washed first with benzene, then with CHCl3. The washings were combined with the initial filtrate and the total concentrated in vacuo to a residue which was chromatographed first on a 20 ml. dry silica gel column (E. Merck 7734) with CHCl3 elution followed by conventional chromatography over 20 g. of silica (E. Merck 7734) packed in benzene-ethyl acetate (95:5) and elution with this solvent mixture provided, after workup, a yellow solid, m.p. 60°-62°.

후처리

  1. temperatureunder reflux for 7 hours
  2. temperaturecooled
  3. customthe formed solid removed by filtration
  4. washThe precipitate was thoroughly washed first with benzene
  5. concentrationthe total concentrated in vacuo to a residue which
  6. customwas chromatographed first on a 20 ml
  7. washdry silica gel column (E. Merck 7734) with CHCl3 elution
  8. washelution with this solvent mixture
  9. customprovided

출처 및 근거

ORD 기록
ord-faaced70dcaa4b2b8d73c3c300f64d98
출처 데이터셋
uspto-grants-1979_04
특허 번호
US04150042

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