Hydrochloric Acid → 2-(Phenethylhydrazono)-propionic acid

HRID 2163684Notes

Reaction equation

HRID 2163684 reaction equation
[CH2:1]([NH:9][N:10]=[C:11]([CH3:17])[C:12]([O:14]CC)=[O:13])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[K+].C(O)C.Cl>C(OCC)C.O>[CH2:1]([NH:9][N:10]=[C:11]([CH3:17])[C:12]([OH:14])=[O:13])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 73183671Ethyl 2-(phenethylhydrazono)-propionate

Product 1

HCID 1942362-(Phenethylhydrazono)-propionic acidYield 47%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

6 g. Ethyl 2-(phenethylhydrazono)-propionate (prepared according to Example 2) are dissolved in a solution of 1.4 g. potassium hydroxide in 28 ml. 80% ethanol and saponified at ambient temperature. After stirring for 30 hours, the reaction mixture is mixed with 25 ml. water and shaken out twice with 50 ml. amounts of diethyl ether. The aqueous phase is acidified with dilute hydrochloric acid. The crystals which precipitate out are filtered off and recrystallized from toluene. There is obtained 2-(phenethylhydrazono)-propionic acid in a yield of 47% of theory; m.p. 74°-76° C.

Workup

  1. customsaponified at ambient temperature
  2. additionthe reaction mixture is mixed with 25 ml
  3. customThe crystals which precipitate out
  4. filtrationare filtered off
  5. customrecrystallized from toluene

Sources & evidence

ORD record
ord-5d37c66fcbf04311a25a4636bf89f1cc
Source dataset
uspto-grants-1979_01
Patent number
US04136196

Reaction notes

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