HCID 23453038, compound → HCID 23453030, compound

HRID 1277666Notes

Reaction equation

HRID 1277666 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([NH:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20]CC)=[O:19])=[CH:13][CH:12]=2)=[O:7])=[CH:4][CH:3]=1>CO.[OH-].[K+]>[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]([CH2:17][C:18]([OH:20])=[O:19])=[CH:13][CH:12]=2)=[O:7])=[CH:23][CH:24]=1

Participants

4

Reactant 1

HCID 23453038HCID 23453038, compound

Product 1

HCID 23453030HCID 23453030, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

13.5 g. ethyl 4-[2-(4-chlorobenzamido)-ethyl]-phenylacetate, dissolved in 110 ml methanol and 39 ml 2 N aqueous potassium hydroxide solution, are maintained at reflux temperature for 12 hours. The solution is then evaporated in a vacuum. After dilution with water, it is extracted with diethyl ether, the aqueous phase is filtered, with the addition of active charcoal, and the filtrate is acidified. There are obtained 11.7 g (95% of theory) of acid which is recrystallized from 25 ml glacial acetic acid. There are obtained 8.2 g (66% of theory) 4-[2-(4-chlorobenzamido)-ethyl]-phenylacetic acid; m.p. 186°-187° C. From the mother liquor, there is obtained a further 1.9 g (15% of theory) of this acid, which has a melting point of 182°-183° C.

Workup

  1. temperatureat reflux temperature for 12 hours
  2. customThe solution is then evaporated in a vacuum
  3. extractionAfter dilution with water, it is extracted with diethyl ether
  4. filtrationthe aqueous phase is filtered, with the addition of active charcoal
  5. customThere are obtained 11.7 g (95% of theory) of acid which
  6. customis recrystallized from 25 ml glacial acetic acid

Sources & evidence

ORD record
ord-7570a43316ad4c22a20af71f16701ed2
Source dataset
uspto-grants-1981_07
Patent number
US04278680

Reaction notes

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