Potassium Hydroxide → HCID 23453101, compound

HRID 1706481Notes

Reaction equation

HRID 1706481 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:28]=[CH:27][C:7]([C:8]([NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH3:26])([CH3:25])[C:20]([O:22]CC)=[O:21])=[CH:15][CH:14]=2)=[O:9])=[CH:6][CH:5]=1>>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH3:25])([CH3:26])[C:20]([OH:22])=[O:21])=[CH:15][CH:14]=2)=[O:9])=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 23453102HCID 23453102, compound

Product 1

HCID 23453101HCID 23453101, compoundYield 96.4%

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-17a01037753942129e103da019be25ce
Source dataset
uspto-grants-1980_06
Patent number
US04207341

Reaction notes

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