Sulfuric Acid → 3,5,6-Trimethyl-2-[phenyl-(3-pyridyl)methyl]-1,4-benzoquinone

HRID 484011

반응식

HRID 484011 반응식
[C:1]1([CH:7]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][C:16]1[C:22]([CH3:23])=[C:21]([OH:24])[C:20]([CH3:25])=[CH:19][C:17]=1[OH:18].S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>ClC(Cl)C>[CH3:25][C:20]1[C:21](=[O:24])[C:22]([CH3:23])=[C:16]([CH3:15])[C:17](=[O:18])[C:19]=1[CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1

참가 물질

6

반응물 4

HCID 1118Sulfuric AcidHCID 12785TrimethylhydroquinoneHCID 234839Phenyl(pyridin-3-yl)methanolHCID 516892Sodium Bicarbonate

생성물 1

HCID 142777673,5,6-Trimethyl-2-[phenyl-(3-pyridyl)methyl]-1,4-benzoquinone수율 72.9%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

to a solution of 1.0 g (5.4 mmol) of phenyl-(3-pyridyl) methanol and 823 mg (5.4 mmol) of 2,3,5-trimethylhydroquinone in 15 ml of dichloroethane, 0.5 ml (9.4 mmol) of concentrated sulfuric acid was added, and refluxed by heating for 2 hours. The reaction mixture was made weakly alkaline with a saturated aqueous solution of sodium hydrogen carbonate, from which the organic phase was separated while the aqueous phase was extracted with chloroform and the extract was combined with the organic phase. The organic phase was washed with water, dried, and oxidized with air, from which the solvent was evaporated off. The residue was purified with silica gel column chromatography (isopropyl ether-ethyl acetate (1:1)), to give 1.25 g (72.7%) of 3,5,6-trimethyl-2-[phenyl-(3-pyridyl)methyl]-1,4-benzoquinone. The physical data are shown in Table 1.

후처리

  1. temperaturerefluxed
  2. temperatureby heating for 2 hours
  3. customfrom which the organic phase was separated while the aqueous phase
  4. extractionwas extracted with chloroform
  5. washThe organic phase was washed with water
  6. customdried
  7. customwas evaporated off
  8. customThe residue was purified with silica gel column chromatography (isopropyl ether-ethyl acetate (1:1))

출처 및 근거

ORD 기록
ord-ba030d7d5b38469aaeafe5928835ec4c
출처 데이터셋
uspto-grants-1993_07
특허 번호
US05229385

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