HCID 11143952, compound → HCID 10959751, compound

HRID 1019402Notes

Reaction equation

HRID 1019402 reaction equation
C[O:2][CH:3]([O:28]C)[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1[C:14](=[O:27])[C:15]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=1>CC(C)=O.O>[CH3:13][O:12][C:7]1[C:8]([O:10][CH3:11])=[CH:9][C:4]([C:3]([OH:28])=[O:2])=[C:5]([C:14](=[O:27])[C:15]2[CH:16]=[C:17]([O:25][CH3:26])[C:18]([O:23][CH3:24])=[C:19]([O:21][CH3:22])[CH:20]=2)[CH:6]=1

Participants

4

Reactant 1

HCID 11143952HCID 11143952, compound

Product 1

HCID 10959751HCID 10959751, compoundYield 1.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

4,5-Dimethoxy-2-(3,4,5-trimethoxybenzoyl)benzaldehyde dimethyl acetal (1.0 g) is dissolved with heating in a mixture of acetone (15 ml) and water (0.5 ml), and thereto is added an acidic ion-exchange resin (IRA-20) (50 nig). The mixture is stirred at room temperature for two hours. After the reaction is complete, the acidic resin is removed by filtration, and the filtrate is concentrated under reduced pressure. The residue is dissolved in dioxane (12 ml), and thereto are added resorcinol (456 nig) and acetate buffer (pH 3.8, 12 ml). To the mixture is added dropwise and gradually aqueous solution of sodium chlorite (374 mg), and the mixture is stirred at room temperature overnight. After the reaction is complete, the pH value of the mixture is adjusted to pH 1 with conc. hydrochloric acid, and the mixture is extracted with chloroform. The chloroform layer is washed, dried, and concentrated under reduced pressure. The precipitated crystals are collected by filtration with diethyl ether to give 4,5-dimethoxy-2-(3,4,5-trimethoxybenzoyl)benzoic acid (8 10 mg) as listed in Table 51.

Workup

  1. additionis added an acidic ion-exchange resin (IRA-20) (50 nig)
  2. customthe acidic resin is removed by filtration
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. dissolutionThe residue is dissolved in dioxane (12 ml)
  5. additionare added resorcinol (456 nig) and acetate buffer (pH 3.8, 12 ml)
  6. additionTo the mixture is added dropwise
  7. stirringgradually aqueous solution of sodium chlorite (374 mg), and the mixture is stirred at room temperature overnight
  8. extractionthe mixture is extracted with chloroform
  9. washThe chloroform layer is washed
  10. customdried
  11. concentrationconcentrated under reduced pressure
  12. filtrationThe precipitated crystals are collected by filtration with diethyl ether

Sources & evidence

ORD record
ord-60d61042047c462b8599ceb10136cc19
Source dataset
uspto-grants-2002_11
Patent number
US06486155B1

Reaction notes

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