Potassium Hydroxide → HCID 23453101, compound

HRID 1277670Notes

Reaction equation

HRID 1277670 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([NH:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([CH3:24])([CH3:23])[C:18]([O:20]CC)=[O:19])=[CH:13][CH:12]=2)=[O:7])=[CH:4][CH:3]=1.[OH-].[K+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([CH3:23])([CH3:24])[C:18]([OH:20])=[O:19])=[CH:13][CH:12]=2)=[O:7])=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 23453102HCID 23453102, compound

Product 1

HCID 23453101HCID 23453101, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

13.9 g ethyl 2-{4-[2-(4-chlorobenzamido)-ethyl]-phenyl}-2-methylpropionate, 100 ml methanol and 37 ml 2 N aqueous potassium hydroxide solution are maintained at reflux temperature for 9 hours, the methanol is then distilled off in a vacuum and the residue is diluted with water and extracted with diethyl ether. The aqueous phase is filtered and acidified. There are obtained 12.8 g (100% of theory) of crude product. After recrystallization from 130 ml glacial acetic acid, there are obtained 12.4 g (94% of theory) 2-{4-[2-(4-chlorobenzamido)-ethyl]-phenyl}-2-methylpropionic acid; m.p. 234°-235° C.

Workup

  1. temperatureat reflux temperature for 9 hours
  2. distillationthe methanol is then distilled off in a vacuum
  3. additionthe residue is diluted with water
  4. extractionextracted with diethyl ether
  5. filtrationThe aqueous phase is filtered
  6. customThere are obtained 12.8 g (100% of theory) of crude product
  7. customAfter recrystallization from 130 ml glacial acetic acid, there

Sources & evidence

ORD record
ord-abd66852b39943a0b95a81013a7223cb
Source dataset
uspto-grants-1981_07
Patent number
US04278680

Reaction notes

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