Sodium Bicarbonate → HCID 22054255, compound

HRID 1830267Notes

Reaction equation

HRID 1830267 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:27])[C:5]([CH3:26])=[C:6]([CH2:12][C:13]2[C:14]([O:22]C(=O)C)=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([OH:18])=[O:17])[C:7](=[O:11])[C:8]=1[O:9][CH3:10].C(=O)([O-])O.[Na+]>CO.O>[CH3:1][O:2][C:3]1[C:4](=[O:27])[C:5]([CH3:26])=[C:6]([CH2:12][C:13]2[C:14]([OH:22])=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([OH:18])=[O:17])[C:7](=[O:11])[C:8]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 22054160HCID 22054160, compound

Product 1

HCID 22054255HCID 22054255, compoundYield 31.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic acid (0.036 g, 0.0963 mmol) was dissolved in methanol (2 ml) and after adding thereto an aqueous saturated sodium hydrogencarbonate solution (2 ml), the solution was stirred at room temperature for 3 hours. After the completion of reaction, the reaction solution was diluted with water and then extracted with ethyl acetate. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by preparative thin-layer chromatography (chloroform:methanol=9:1) and then recrystallized from diisopropyl ether to obtain the titled compound (0.010 g, 0.0301 mmol, 31%).

Workup

  1. additionafter adding
  2. customAfter the completion of reaction
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. customthe solvent was removed by distillation
  7. customThe obtained residue was purified by preparative thin-layer chromatography (chloroform:methanol=9:1)
  8. customrecrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-12c6eab000b6427ba2f99d399ecaf1f6
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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