Water → {[3-(4-Chlorophenyl)-1,2-benzisoxazol-6-yl]oxy}-acetic acid

HRID 652933Notes

Reaction equation

HRID 652933 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]([OH:17])=[CH:16][C:11]=3[O:10][N:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:21][C:22]([O:24]CC)=[O:23].O>CN(C)C=O>[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][CH2:21][C:22]([OH:24])=[O:23])=[CH:16][C:11]=3[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 1355896553-(4-Chloro-phenyl)-benzo[D]isoxazol-6-OL

Product 1

HCID 14012528{[3-(4-Chlorophenyl)-1,2-benzisoxazol-6-yl]oxy}-acetic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 5.3 g of 3-(4-chlorophenyl)-6-hydroxy-1,2-benzisoxazole in 30 ml of dimethylformamide is added dropwise to a suspension of 0.65 g of sodium hydride (50% suspension in oil) in 30 ml of dimethylformamide. After stirring for 20 min, 1.4 ml of ethyl bromoacetate is added. The reaction mixture is stirred for 1 hr, poured into water and the precipitate is collected. The precipitate is added to 30 ml of 15% sodium hydroxide solution and 30 ml methanol and heated at reflux for 3 hr. The mixture is poured into water, acidified and filtered. Recrystallization from toluene and acetonitrile gives {[3-(4-chlorophenyl)-1,2-benzisoxazol-6-yl]oxy}-acetic acid, mp 207° C.

Workup

  1. stirringThe reaction mixture is stirred for 1 hr
  2. customthe precipitate is collected
  3. additionThe precipitate is added to 30 ml of 15% sodium hydroxide solution and 30 ml methanol
  4. temperatureheated
  5. temperatureat reflux for 3 hr
  6. additionThe mixture is poured into water
  7. filtrationfiltered
  8. customRecrystallization from toluene and acetonitrile

Sources & evidence

ORD record
ord-2643b3a4c36e41b6acdbdb9c220868aa
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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