4-[3,5,6-Trimethyl-1,4-benzoquinon-2-yl(3-pyridyl)methyl]-alpha-methylcinnamic acid → 3-(4-[3,5,6-Trimethyl-1,4-benzoquinon-2-yl-(3-pyridyl)methyl]phenyl)propionic acid

HRID 703934Notes

Reaction equation

HRID 703934 reaction equation
[CH3:1][C:2]1[C:7](=[O:8])[C:6]([CH3:9])=[C:5]([CH3:10])[C:4](=[O:11])[C:3]=1[CH:12]([C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1)[C:13]1[CH:24]=[CH:23][C:16]([CH:17]=[C:18](C)[C:19]([OH:21])=[O:20])=[CH:15][CH:14]=1>C(O)(=O)C.[Pd].[C]>[CH3:1][C:2]1[C:7](=[O:8])[C:6]([CH3:9])=[C:5]([CH3:10])[C:4](=[O:11])[C:3]=1[CH:12]([C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1)[C:13]1[CH:24]=[CH:23][C:16]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:15][CH:14]=1

Participants

4

Reactant 1

HCID 571128964-[3,5,6-Trimethyl-1,4-benzoquinon-2-yl(3-pyridyl)methyl]-alpha-methylcinnamic acid

Product 1

HCID 142777693-(4-[3,5,6-Trimethyl-1,4-benzoquinon-2-yl-(3-pyridyl)methyl]phenyl)propionic acidYield 44.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

4-[3,5,6-trimethyl-1,4-benzoquinon-2-yl-(3-pyridyl)methyl]-α-methylcinnamic acid, 0.7 g (1.75 mmol), was hydrogenated with 0.2 g of 5% Pd-carbon in 6 ml of acetic acid (the reaction completed in about 2 hours). The catalyst was filtered off, and the filtrate was concentrated, to which water was added and neutralized with a saturated aqueous solution of sodium hydrogen carbonate. The resultant substance was extracted with ethyl acetate, and oxidized by shaking with an aqueous solution of ferric chloride. After the organic phase was washed with water and dried, the solvent was evaporated off and the residue was purified with silica gel column chromatography (ethyl acetate-ethanol (9:1)) and recrystallized from ethyl acetate, to give 0.3 g (44.2%) of 3-(4-[3,5,6-trimethyl-1,4-benzoquinon-2-yl-(3-pyridyl)methyl]phenyl)propionic acid. The physical data are shown in Table 1.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated, to which water
  3. additionwas added
  4. extractionThe resultant substance was extracted with ethyl acetate
  5. washAfter the organic phase was washed with water
  6. customdried
  7. customthe solvent was evaporated off
  8. customthe residue was purified with silica gel column chromatography (ethyl acetate-ethanol (9:1))
  9. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3e2b6469fba34850b46eedae8893328b
Source dataset
uspto-grants-1991_01
Patent number
US04985447

Reaction notes

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