Hydrochloric Acid → HCID 13015752, compound

HRID 652863Notes

Reaction equation

HRID 652863 reaction equation
C([O:3][C:4](=[O:25])[CH2:5][O:6][C:7]1[CH:23]=[CH:22][C:10]2[C:11]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=3)=[N:12][O:13][C:9]=2[C:8]=1[Cl:24])C.O.Cl>C(O)C.[OH-].[Na+]>[Cl:24][C:8]1[C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=3)[C:10]=2[CH:22]=[CH:23][C:7]=1[O:6][CH2:5][C:4]([OH:25])=[O:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 14012494HCID 14012494, compound

Product 1

HCID 13015752HCID 13015752, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a suspension of 19 g of the ester in 400 ml of ethanol, 20 ml of 50% NaOH is added. A precipitate forms and the heterogeneous mixture is refluxed for 1 hour. To the hot mixture 400 ml of water is added followed by concentrated HCl until the mixture is acidic. The suspension is stirred one half hour, filtered and recrystallized from DMF-ethylacetate to give {[7-chloro-3-(3,4-dichlorophenyl)-1,2-benzisoxazol-6-yl]oxy}acetic acid, mp 222°-224° C.

Workup

  1. additionis added
  2. temperatureA precipitate forms and the heterogeneous mixture is refluxed for 1 hour
  3. filtrationfiltered
  4. customrecrystallized from DMF-ethylacetate

Sources & evidence

ORD record
ord-08e6868502cf4e06bd009a8ee8879b6a
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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