Sodium Hydroxide → 2-{[3-(4-Chlorophenyl)-1,2-benzisoxazol-6-yl]oxy}pentanoic acid

HRID 652943Notes

Reaction equation

HRID 652943 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([O:17][CH:18]([CH2:24][CH2:25][CH3:26])[C:19]([O:21]CC)=[O:20])=[CH:16][C:11]=3[O:10][N:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([O:17][CH:18]([CH2:24][CH2:25][CH3:26])[C:19]([OH:21])=[O:20])=[CH:16][C:11]=3[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14012537Ethyl 2-{[3-(4-chlorophenyl)-1,2-benzisoxazol-6-yl]oxy}pentanoate

Product 1

HCID 140125382-{[3-(4-Chlorophenyl)-1,2-benzisoxazol-6-yl]oxy}pentanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3.5 g of ethyl 2-{[3-(4-chlorophenyl)-1,2-benzisoxazol-6-yl]oxy}pentanoate, 30 ml 15% sodium hydroxide and 30 ml methanol is heated under reflux for 1.5 hr. The reaction mixture is poured into ice/dil hydrochloric acid with stirring. The precipitate is collected, washed with water and dried in vacuo. Recrystallization from toluene/acetonitrile affords 2-{[3-(4-chlorophenyl)-1,2-benzisoxazol-6-yl]oxy}pentanoic acid, mp 170° C.

Workup

  1. temperatureunder reflux for 1.5 hr
  2. customThe precipitate is collected
  3. washwashed with water
  4. customdried in vacuo
  5. customRecrystallization from toluene/acetonitrile

Sources & evidence

ORD record
ord-fbae3341665d47fb8eaefc441003b772
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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