Water → HCID 14128056, compound

HRID 414345Notes

Reaction equation

HRID 414345 reaction equation
[CH3:1][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]>[CH3:1][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:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:6]=2[CH:16]=1

Participants

6

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 14128055HCID 14128055, compound

Product 1

HCID 14128056HCID 14128056, compoundYield 61.4%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolvent

Procedure

A portion (4.5 g) of the 7,8-dihydro-5-methyl-3-phenylfuro[2,3-g]-1,2-benzisoxazole-7-methanol prepared in Example 9 was dissolved in 150 ml of acetone. To the stirred solution, a mixture of chromium (VI) oxide (5.9 g), water (12 ml) and concentrated sulfuric acid (8.3 g) was added dropwise over time, and the resulting mixture was stirred for 2 hours at room temperature. After leaving the mixture to stand overnight, 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 to yield 2.9 g of 7,8-dihydro-5-methyl-3-phenylfuro[2,3-g]-1,2-benzisoxazole-7carboxylic acid. m.p. 210°-213° C. This compound exhibited a mass spectrum haivng a molecular ion peak at m/e 295.

Workup

  1. additionwas added dropwise over time
  2. customAfter leaving the mixture
  3. waitto stand overnight
  4. filtrationthe insolubles were filtered off by suction
  5. distillationAfter distilling off the acetone, water
  6. additionwas added
  7. extractionthe mixture was subjected to extraction with ether
  8. washThe ether layer was washed with water
  9. customdried
  10. distillationAfter distilling off the solvent
  11. customthe residue was recrystallized from acetone-water

Sources & evidence

ORD record
ord-c261748f8d00413393d313aeb7276cde
Source dataset
uspto-grants-1988_12
Patent number
US04791209

Reaction notes

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