Water → HCID 14128052, compound

HRID 414342Notes

Reaction equation

HRID 414342 reaction equation
[Br:1][C:2]1[C:3]2[O:19][CH:18]([CH2:20][OH:21])[CH2:17][C:4]=2[C:5]2[O:9][N:8]=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:6]=2[CH:16]=1.O.S(=O)(=O)(O)[OH:24]>CC(C)=O.[O-2].[Cr+6].[O-2].[O-2]>[Br:1][C:2]1[C:3]2[O:19][CH:18]([C:20]([OH:24])=[O:21])[CH2:17][C:4]=2[C:5]2[O:9][N:8]=[C:7]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:6]=2[CH:16]=1

Participants

6

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 143487705-Bromo-7,8-dihydro-3-phenylfuro[2,3-g]-1,2-benzisoxazole-7-methanol

Product 1

HCID 14128052HCID 14128052, compoundYield 54.9%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolvent

Procedure

A portion (0.7 g) of the 5-bromo-7,8-dihydro-3-phenylfuro[2,3-g]-1,2-benzisoxazole-7-methanol prepared in Example 4 was dissolved in 50 ml of acetone. To the stirred solution, a mixture of chromium (VI) oxide (1 g), water (3 ml) and concentrated sulfuric acid (1.4 g) was added dropwise over time, and the solution was stirred for 6 hours at room temperature. The insolubles were filtered off by suction. After distilling off the acetone, water was added to the residue 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 with acetone-water, yielding 0.4 g of 5-bromo-7,8-dihydro-3-phenylfuro[2,3-g]-1,2-benzisoxazole-7-carboxylic acid. m.p. 241.5°-243.5° C. (with decomposition).

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 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 with acetone-water

Sources & evidence

ORD record
ord-5e34e890d803414c99396c94087c791a
Source dataset
uspto-grants-1988_12
Patent number
US04791209

Reaction notes

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