Water → HCID 14128060, compound

HRID 414349Notes

Reaction equation

HRID 414349 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[Cl: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[Cl:16])[C:6]=2[CH:17]=1

Participants

6

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 14128059HCID 14128059, compound

Product 1

HCID 14128060HCID 14128060, compoundYield 55.5%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolvent

Procedure

A portion (4.5 g) of the 5-chloro-3-(2-chlorophenyl)7,8-dihydrofuro[2,3-g]-1,2-benzisoxazole-7-methanol prepared in Example 13 was dissolved in 200 ml of acetone. To the stirred solution, a mixture of chromium (VI) oxide (4.9 g), water (10 ml) and concentrated sulfuric acid (6.9 g) was added dropwise over time, and the resulting mixture was stirred for 8 hours at room temperature. The insolubles were filtered off by suction. After distilling off the acetone, water was added to the residue and the solution 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 2.6 g of 5-chloro-3-(2-chlorophenyl)-7,8-dihydrofuro[2,3-g]-1,2-benzisoxazole-7-carboxylic acid. m.p. 220°-221.5° C. This compound exhibited a mass spectrum having a molecular ion peak at m/e 349.

Workup

  1. additionwas added dropwise over time
  2. filtrationThe insolubles were filtered off by suction
  3. distillationAfter distilling off the acetone, water
  4. additionwas added to the residue
  5. extractionthe solution 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-4e397c37b88944e78964457f40dea924
Source dataset
uspto-grants-1988_12
Patent number
US04791209

Reaction notes

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