Water → HCID 14128058, compound

HRID 414347Notes

Reaction equation

HRID 414347 reaction equation
[Cl:1][C:2]1[C:3]2[O:20][CH:19]([CH2:21][OH:22])[CH2:18][C:4]=2[C:5]2[O:9][N:8]=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[F:16])[C:6]=2[CH:17]=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:3]2[O:20][CH:19]([C:21]([OH:25])=[O:22])[CH2:18][C:4]=2[C:5]2[O:9][N:8]=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[F:16])[C:6]=2[CH:17]=1

Participants

6

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 14128057HCID 14128057, compound

Product 1

HCID 14128058HCID 14128058, compoundYield 89.8%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolvent

Procedure

A portion (6.4 g) of the 5-chloro-7,8-dihydro-3-(2-fluorophenyl)furo[2,3-g]-1,2-benzisoxazole-7-methanol prepared in Example 11 was dissolved in 150 ml of acetone. To the stirred solution, a mixture of chromium (VI) oxide (7.2 g), water (15 ml) and concentrated sulfuric acid (10.2 g) was added dropwise overtime, and the mixture was agitated for 8 hours at room temperature. The insolubles were filtered off by suction. After distilling off the acetone, water was added and the mixture was subjected to extraction with ether. The ether layer was washed with water and dried. After distilling off the solvent, the residue was recrystallized from acetone-water, yielding 6.0 g of 5-chloro-7,8-dihydro-3-(2-fluorophenyl)furo[2,3-g]-1,2-benzisoxazole-7-carboxylic acid. m.p. 199°-200° C. This compound exhibited a mass spectrum having a molecular ion peak at m/e 333.

Workup

  1. additionwas added dropwise overtime
  2. filtrationThe insolubles were filtered off by suction
  3. distillationAfter distilling off the acetone, water
  4. additionwas added
  5. extractionthe mixture was subjected to extraction with ether
  6. washThe ether layer was washed with water
  7. customdried
  8. distillationAfter distilling off the solvent
  9. customthe residue was recrystallized from acetone-water

Sources & evidence

ORD record
ord-a58e9ba590d84961b771912ee7972c33
Source dataset
uspto-grants-1988_12
Patent number
US04791209

Reaction notes

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