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

HRID 484011

Reaction equation

HRID 484011 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

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.

Workup

  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))

Sources & evidence

ORD record
ord-ba030d7d5b38469aaeafe5928835ec4c
Source dataset
uspto-grants-1993_07
Patent number
US05229385

Linked notes

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