Hydrochloric Acid → HCID 13982862, compound

HRID 569473Notes

Reaction equation

HRID 569473 reaction equation
[OH:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[N:7][O:8][C:4]=2[C:3]=1[OH:17].C(=O)([O-])[O-].[K+].[K+].Cl[CH:25](Cl)[C:26]([O:28]C)=[O:27].Cl>O.CN(C)C=O>[C:9]1([C:6]2[C:5]3[CH:15]=[CH:16][C:2]4[O:1][CH:25]([C:26]([OH:28])=[O:27])[O:17][C:3]=4[C:4]=3[O:8][N:7]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8315Methyl dichloroacetateHCID 11430Potassium CarbonateHCID 135589618HCID 135589618, compound

Product 1

HCID 13982862HCID 13982862, compoundYield 57.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 6,7-dihydroxy-3-phenyl-1,2-benzisoxazole (2.1 g), potassium carbonate (7.7 g), methyl dichloroacetate (2.7 g) and N,N-dimethylformamide (50 ml) was stirred at 90°-100° C. for 5 hours. After addition of water (100 ml), the mixture was stirred at 90°-100° C. for 30 minutes, and after acidifying it with hydrochloric acid, 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 1.5 g of 3-phenyl-1,3-dioxolo[4,5-g]-1,2-benzisoxazole-7-carboxylic acid. m.p.: 187°-190° C.

Workup

  1. stirringthe mixture was stirred at 90°-100° C. for 30 minutes
  2. extractionextracted with ether
  3. washThe ether layer was washed with water
  4. customdried
  5. customevaporated
  6. customto remove the solvent
  7. customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-0bbf76c2d98c4a22a56ea4946d52116a
Source dataset
uspto-grants-1988_03
Patent number
US04732906

Reaction notes

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