Water → HCID 23709655, compound

HRID 569472Notes

Reaction equation

HRID 569472 reaction equation
[OH:1][C:2]1[C:3]([OH:18])=[CH:4][C:5]2[O:9][N:8]=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[CH3:16])[C:6]=2[CH:17]=1.C(=O)([O-])[O-].[K+:23].[K+].Cl[CH:26](Cl)[C:27]([O:29]C)=[O:28].O>CN(C)C=O>[K+:23].[C:11]1([CH3:16])[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:7]1[C:6]2[CH:17]=[C:2]3[O:1][CH:26]([C:27]([O-:29])=[O:28])[O:18][C:3]3=[CH:4][C:5]=2[O:9][N:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8315Methyl dichloroacetateHCID 11430Potassium CarbonateHCID 135589617105679-44-5

Product 1

HCID 23709655HCID 23709655, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5,6-dihydroxy-3-(o-tolyl)-1,2-benzisoxazole (4.7 g), potassium carbonate (12.1 g), methyl dichloroacetate (4.2 g) in N,N-dimethylformamide (40 ml) was stirred at 90°-95° C. for 1.5 hours. After cooling, water (10 ml) was added to the mixture followed by stirring at 80°-90° C. for 10 minutes. After cooling the mixture was extracted with ether, and then the ether layer was washed with water, dried and evaporated to remove the solvent. The residue was dissolved in a potassium bicarbonate aqueous solution, and then ethanol was added to the solution. The resulting precipitate was collected by filtration, washed with ethanol and dried in air to give 3.1 g of 3-(o-tolyl)-1,3-dioxolo [4,5-f]-1,2-benzisoxazole-6-carboxylic acid potassium salt. The resulting potassium salt was dissolved in a small amount of water, and after acidifying it with hydrochloric acid, was extracted with ether. The ether layer was washed with water, dried and evaporated to remove the solvent. The residue was recrystallized from acetonitrile to give 1.9 g of 3-(o-tolyl)-1,3-dioxolo[4,5-f]-1,2-benzisoxazole-6-carboxylic acid. m.p.: 166-170 (decomposition)

Workup

  1. temperatureAfter cooling
  2. stirringby stirring at 80°-90° C. for 10 minutes
  3. temperatureAfter cooling the mixture
  4. extractionwas extracted with ether
  5. washthe ether layer was washed with water
  6. customdried
  7. customevaporated
  8. customto remove the solvent
  9. dissolutionThe residue was dissolved in a potassium bicarbonate aqueous solution
  10. additionethanol was added to the solution
  11. filtrationThe resulting precipitate was collected by filtration
  12. washwashed with ethanol
  13. customdried in air

Sources & evidence

ORD record
ord-a373d39e50a64e659b5270d90fbc373c
Source dataset
uspto-grants-1988_03
Patent number
US04732906

Reaction notes

Loading…