Hydrochloric Acid → L-Alanine, N-(2,6-dimethylphenyl)-

HRID 894850Notes

Reaction equation

HRID 894850 reaction equation
[OH-].[K+].C[O:4][C:5](=[O:17])[C@H:6]([CH3:16])[NH:7][C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:15].Cl>CO>[CH3:14][C:13]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:15])[C:8]=1[NH:7][C@H:6]([C:5]([OH:17])=[O:4])[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 11481178HCID 11481178, compound

Product 1

HCID 158332L-Alanine, N-(2,6-dimethylphenyl)-Yield 68.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,000 ml (2 mol) of 2 molar methanolic potassium hydroxide solution were added to a solution of 207 g (1 mol) of N-(2,6-dimethylphenyl)-alanine methyl ester in 1,000 ml of methanol and the mixture was heated under reflux for 3 hours. After cooling, the reaction solution was acidified with 190 ml of concentrated hydrochloric acid, the potassium chloride which had precipitated was filtered off and the filtrate was evaporated in vacuo. The oily residue crystallized on grinding and warming with 350 ml of ethyl acetate and 100 ml of petroleum ether. 133 g (68% of theory) of N-(2,6-dimethylphenyl)-alanine with a melting point of 178°-180° C. were obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling
  4. customthe potassium chloride which had precipitated
  5. filtrationwas filtered off
  6. customthe filtrate was evaporated in vacuo
  7. customThe oily residue crystallized
  8. customon grinding
  9. temperaturewarming with 350 ml of ethyl acetate and 100 ml of petroleum ether

Sources & evidence

ORD record
ord-504d522ee7604505bc97ec1bbbed50de
Source dataset
uspto-grants-1981_08
Patent number
US04284791

Reaction notes

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