Water → HCID 14128069, compound

HRID 414356Notes

Reaction equation

HRID 414356 reaction equation
[Cl:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])=[N:9][O:10][C:6]=2[C:5]2[CH2:18][CH:19]([CH2:21][OH:22])[O:20][C:4]=2[CH:3]=1.O.S(=O)(=O)(O)[OH:25]>CC(C)=O.[O-2].[Cr+6].[O-2].[O-2]>[Cl:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])=[N:9][O:10][C:6]=2[C:5]2[CH2:18][CH:19]([C:21]([OH:25])=[O:22])[O:20][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 14128068HCID 14128068, compound

Product 1

HCID 14128069HCID 14128069, compoundYield 60.2%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolvent

Procedure

A portion (4.3 g) of the 4-chloro-7,8-dihydro-3-(2-fluorophenyl)furo[2,3-g]-1,2-benzisoxazole-7-methanol obtained in Example 22 was dissolved in 120 ml of acetone. To the solution, a mixture of chromium (VI) oxide (6.5 g), water (15 ml) and concentrated sulfuric acid (9.3 g) was added dropwise under stirring. The stirring was continued at room temperature for 2 hours, then the mixture was left to stand overnight. The insolubles were filtered off by suction, and the solvent was distilled off. Water was added to the residue, followed by extraction with ether. The ether layer was washed with water and dried, and the solvent was distilled off. The residue was recrystallized from acetone/water to yield 2.7 g of 4-chloro-7,8-dihydro-3-(2-fluorophenyl)furo[2,3-g]-1,2-benzisoxazole-7-carboxylic acid. m.p. 191°-193° C.

Workup

  1. additionwas added dropwise
  2. waitthe mixture was left
  3. waitto stand overnight
  4. filtrationThe insolubles were filtered off by suction
  5. distillationthe solvent was distilled off
  6. additionWater was added to the residue
  7. extractionfollowed by extraction with ether
  8. washThe ether layer was washed with water
  9. customdried
  10. distillationthe solvent was distilled off
  11. customThe residue was recrystallized from acetone/water

Sources & evidence

ORD record
ord-213c03b9562949f798d62a4df4cf7440
Source dataset
uspto-grants-1988_12
Patent number
US04791209

Reaction notes

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