Water → HCID 14128055, compound

HRID 414344Notes

Reaction equation

HRID 414344 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]=[C:6]([CH3:19])[C:5]=1[OH:20])[CH:2]=[CH2:3].ClC1C=CC=C(C(OO)=[O:29])C=1.O.[OH-].[Na+]>C(Cl)Cl>[CH3:19][C:6]1[C:5]2[O:20][CH:2]([CH2:3][OH:29])[CH2:1][C:4]=2[C:12]2[O:11][N:10]=[C:9]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:8]=2[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 135583516HCID 135583516, compound

Product 1

HCID 14128055HCID 14128055, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the ice-cooled solution of 7-allyl-6-hydroxy-5-methyl-3-phenyl-1,2-benzisoxazole (4.5 g) in methylene chloride (200 ml), 7.6 g of m-chloroperbenzoic acid was added in small portions under agitation, and the solution was subsequently refluxed for 3 hours. After cooling the solution, water and 50 ml of an aqueous solution of 2N sodium hydroxide 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, 4.6 g of 7,8-dihydro-5-methyl3-phenylfuro[2,3-g]-1,2-benzisoxazole-7-methanol was obtained. m.p. 130°-133° C. This compound exhibited a mass spectrum having a molecular ion peak at m/e 281.

Workup

  1. additionwas added in small portions under agitation
  2. temperaturethe solution was subsequently refluxed for 3 hours
  3. additionwere added
  4. extractionthe mixture was subjected to extraction 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-a1edf23f158946e3844dac3258beea2b
Source dataset
uspto-grants-1988_12
Patent number
US04791209

Reaction notes

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