Water → HCID 14128049, compound

HRID 414339Notes

Reaction equation

HRID 414339 reaction equation
[CH2:1]([C:4]1[C:12]2[O:11][N:10]=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8]=2[CH:7]=[CH:6][C:5]=1[OH:19])[CH:2]=[CH2:3].ClC1C=CC=C(C(OO)=[O:28])C=1.O.[OH-].[Na+]>C(Cl)Cl>[C:13]1([C:9]2[C:8]3[CH:7]=[CH:6][C:5]4[O:19][CH:2]([CH2:3][OH:28])[CH2:1][C:4]=4[C:12]=3[O:11][N:10]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 135583513HCID 135583513, compound

Product 1

HCID 14128049HCID 14128049, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of 7-allyl-6-hydroxy-3-phenyl-1,2-benzisoxazole (17.5 g) in methylene chloride (500 ml), m-chloroperbenzoic acid (20.8 g) was added in small portions under agitation, and the mixture was refluxed for 4 hours. After cooling the mixture, water and an aqueous solution of 2N sodium hydroxide (80 ml) were added and the mixture was subjected to extraction with methylene chloride. The methylene chloride layer was washed with water and dried. By distilling off the solvent, 18 g of 7,8-dihydro-3-phenylfuro[2,3-g]-1,2-benzisoxazole-7-methanol was obtained. m.p. 107°-109° C. This compound exhibited a mass spectrum having a molecular ion peak at m/e 267.

Workup

  1. additionwas added in small portions under agitation
  2. temperaturethe mixture was refluxed for 4 hours
  3. extractionthe mixture was subjected to extraction with methylene chloride
  4. washThe methylene chloride layer was washed with water
  5. customdried
  6. distillationBy distilling off the solvent

Sources & evidence

ORD record
ord-003728f738274e7b8033457006ebf4d3
Source dataset
uspto-grants-1988_12
Patent number
US04791209

Reaction notes

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