Water → HCID 14128050, compound

HRID 414340Notes

Reaction equation

HRID 414340 reaction equation
[C:1]1([C:7]2[C:11]3[CH:12]=[CH:13][C:14]4[O:18][CH:17]([CH2:19][OH:20])[CH2:16][C:15]=4[C:10]=3[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.S(=O)(=O)(O)[OH:23]>CC(C)=O.[O-2].[Cr+6].[O-2].[O-2]>[C:1]1([C:7]2[C:11]3[CH:12]=[CH:13][C:14]4[O:18][CH:17]([C:19]([OH:23])=[O:20])[CH2:16][C:15]=4[C:10]=3[O:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 14128049HCID 14128049, compound

Product 1

HCID 14128050HCID 14128050, compoundYield 43.2%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolvent

Procedure

A portion (5.5 g) of the 7,8-dihydro-3-phenylfuro[2,3-g]-1,2-benzisoxazole-7-methanol prepared in Example 1 was dissolved in 200 ml of acetone. To the stirred solution, a mixture of chromium (VI) oxide (10 g), water (20 ml) and concentrated sulfuric acid (16 g) was added dropwise over time, and the solution was left to stand overnight. 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 ethyl acetate. The ethyl acetate layer was washed with water and dried, followed by distilling off the solvent. The residue was recrystallized with acetonitrile to yield 2.5 g of 7,8-dihydro-3-phenylfuro[2,3-g]-1,2-benzisoxazole-7-carboxlic acid. m.p. 219°-220° C. This compound exhibited a mass spectrum having a molecular ion peak at m/e 281.

Workup

  1. additionwas added dropwise over time
  2. waitthe solution was left
  3. filtrationThe insolubles were filtered off by suction
  4. distillationAfter distilling off the acetone, water
  5. additionwas added to the residue
  6. extractionthe mixture was subjected to extraction with ethyl acetate
  7. washThe ethyl acetate layer was washed with water
  8. customdried
  9. distillationby distilling off the solvent
  10. customThe residue was recrystallized with acetonitrile

Sources & evidence

ORD record
ord-59e12ce4ff00471bb7c643fdb3da71d8
Source dataset
uspto-grants-1988_12
Patent number
US04791209

Reaction notes

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