Water → HCID 14128059, compound

HRID 414348Notes

Reaction equation

HRID 414348 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][C:14]=3[Cl:19])[C:8]=2[CH:7]=[C:6]([Cl:20])[C:5]=1[OH:21])[CH:2]=[CH2:3].ClC1C=CC=C(C(OO)=[O:30])C=1.O.[OH-].[Na+]>C(Cl)Cl>[Cl:20][C:6]1[C:5]2[O:21][CH:2]([CH2:3][OH:30])[CH2:1][C:4]=2[C:12]2[O:11][N:10]=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[C:8]=2[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 135583515HCID 135583515, compound

Product 1

HCID 14128059HCID 14128059, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the ice-cooled solution of 7-allyl-5-chloro-3-(2-chlorophenyl)-6-hydroxy-1,2-benzisoxazole (4.5 g) in methylene chloride (200 ml), 6.6 g of m-chloroperbenzoic acid was added in small portions under agitation, and the mixture was subsequently refluxed for 4 hours. After cooling the mixture, water and 50 ml of an aqueous solution of 2N sodium hydroxide were added and the mixture was extracted with methylene chloride. The methylene chloride layer was washed with water and dried. By distilling off the solvent, 4.6 g of 5-chloro-3-(2-chlorophenyl)-7,8-dihydrofuro[2,3-g]-1,2-benzisoxazole-7-methanol was obtained. m.p. 162°-163° C. This compound exhibited a mass spectrum having a molecular ion peak at m/e 335.

Workup

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

Sources & evidence

ORD record
ord-30c930d5a0be4159a0654d0289a3fa18
Source dataset
uspto-grants-1988_12
Patent number
US04791209

Reaction notes

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