Chloroacetic Acid → 2-(Benzylamino)acetic acid

HRID 1709356Notes

Reaction equation

HRID 1709356 reaction equation
[C:1]([NH:9]O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:12][C:13]([OH:15])=[O:14].[OH-].[Na+]>CO>[CH2:1]([NH:9][CH2:12][C:13]([OH:15])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 10313Benzohydroxamic acidHCID 14798Sodium Hydroxide

Product 1

HCID 869652-(Benzylamino)acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

13.7 Grams (0.1 mole) of benzhydroxamic acid and 8.8 g (0.1 mole) of chloroacetic acid were dissolved in 60 ml of methyl alcohol. To the resulting solution, 20 g (0.2 moles) of 40% aqueous solution of sodium hydroxide was slowly added dropwise. After completion of the addition, the reaction solution was heated under reflux for 8 hours and subsequently cooled. After distilling of methyl alcohol under vacuum, concentrated hydrochloric acid was added to the remaining aqueous solution so as to adjust pH to 1. Ethyl acetate (50 ml) was added to the solution. The separated organic layer was washed twice with 50 ml of a saturated sodium chloride solution. By distilling off ethyl acetate, benzamidooxyacetic acid (m.p. 144°145° C.) was obtained in an amount of 18.2 g (yield, 93 mol %).

Workup

  1. additionAfter completion of the addition
  2. temperaturethe reaction solution was heated
  3. temperatureunder reflux for 8 hours
  4. temperaturesubsequently cooled
  5. distillationAfter distilling of methyl alcohol under vacuum, concentrated hydrochloric acid
  6. additionwas added to the remaining aqueous solution so as
  7. additionEthyl acetate (50 ml) was added to the solution
  8. washThe separated organic layer was washed twice with 50 ml of a saturated sodium chloride solution
  9. distillationBy distilling off ethyl acetate

Sources & evidence

ORD record
ord-88b4605402b541bc927cf8421cc13aa4
Source dataset
uspto-grants-1990_08
Patent number
US04948916

Reaction notes

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