Lactic Acid → 1-Carboxyethyl 4-(allylamino)phenylacetate

HRID 1278313Notes

Reaction equation

HRID 1278313 reaction equation
[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[C:15]([OH:20])(=[O:19])[CH:16]([CH3:18])O.C1(C)C(S(O)(=O)=O)=CC=CC=1>C1(C)C=CC=CC=1>[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH:16]([C:15]([OH:20])=[O:19])[CH3:18])=[O:13])=[CH:7][CH:6]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 612Lactic AcidHCID 69252-Methylbenzenesulfonic acidHCID 38316Acetic acid, 2-(p-(allylamino)phenyl)-

Product 1

HCID 211634791-Carboxyethyl 4-(allylamino)phenylacetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A flask containing 10.0 g. 4-(allylamino)phenylacetic acid, 3.3 g. lactic acid, 500 mg. toluenesulfonic acid and 500 ml. toluene equipped with a Soxhlet extractor charged with activated 4 A Linde molecular sieves. The solution is refluxed for 24 hours during which time the Soxhlet extractor is charged twice more with fresh sieves. The hot solution is filtered and left to cool, whereupon 1-carboxyethyl 4-(allylamino)phenylacetate separates as off-white crystals.

Workup

  1. additionA flask containing 10.0 g
  2. additioncharged
  3. temperatureThe solution is refluxed for 24 hours during which time the Soxhlet extractor
  4. additionis charged twice more with fresh sieves
  5. filtrationThe hot solution is filtered
  6. waitleft
  7. temperatureto cool, whereupon 1-carboxyethyl 4-(allylamino)phenylacetate

Sources & evidence

ORD record
ord-6622ab184a5541cfa3a43ead1ecfb10d
Source dataset
uspto-grants-1981_07
Patent number
US04281019

Reaction notes

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