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

HRID 1030591Notes

Reaction equation

HRID 1030591 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:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)[C:13]1[CH:26]=[CH:25][C:16]([CH:17]=[C:18]([CH3:24])[C:19]([O:21]CC)=[O:20])=[CH:15][CH:14]=1.C(=O)([O-])O.[Na+]>Cl>[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:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)[C:13]1[CH:26]=[CH:25][C:16]([CH:17]=[C:18]([CH3:24])[C:19]([OH:21])=[O:20])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 57139798Ethyl 4-[3,5,6-trimethyl-1,4-benzoquinon-2-yl(3-pyridyl)methyl]-alpha-methylcinnamate

Product 1

HCID 571128964-[3,5,6-Trimethyl-1,4-benzoquinon-2-yl(3-pyridyl)methyl]-alpha-methylcinnamic acidYield 85.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Ethyl 4-[3,5,6-trimethyl-1,4-benzoquinon-2-yl-(3-pyridyl)methyl]-α-methylcinnamate, 1.2 g (2.8 mmol), was dissolved in 20 ml of concentrated hydrochloric acid, and refluxed by heating for 2 hours. After cooling, the reaction mixture was neutralized with a saturated aqueous solution of sodium hydrogen carbonate, and the resulting substance was extracted with ethyl acetate. The extract was washed with water and dried, and the solvent was evaporated off. The residue was purified with silica gel column chromatography (ethyl acetate-ethanol (9:1)), and recrystallized from ethyl acetate, to give 0.96 g (85.6%) of 4-[3,5,6-trimethyl-1,4-benzoquinon-2-yl(3-pyridyl)methyl]-α-methylcinnamic acid. The physical data are shown in Table 1.

Workup

  1. temperaturerefluxed
  2. temperatureby heating for 2 hours
  3. temperatureAfter cooling
  4. extractionthe resulting substance was extracted with ethyl acetate
  5. washThe extract 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-e3ff34fc3ebf473780092f56da5ff377
Source dataset
uspto-grants-1992_04
Patent number
US05106858

Reaction notes

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