Lactic Acid → 1-Carboxyethyl 4-(hexadecylamino)benzoate

HRID 1680288Notes

Reaction equation

HRID 1680288 reaction equation
[CH2:1]([NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[C:27]([OH:32])(=[O:31])[CH:28]([CH3:30])O.C1(C)C(S(O)(=O)=O)=CC=CC=1>C1(C)C=CC=CC=1>[CH2:1]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([O:24][CH:28]([C:27]([OH:32])=[O:31])[CH3:30])=[O:23])=[CH:25][CH:26]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 612Lactic AcidHCID 69252-Methylbenzenesulfonic acidHCID 472634-(Hexadecylamino)benzoic acid

Product 1

HCID 234578601-Carboxyethyl 4-(hexadecylamino)benzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A flask containing 10.0 g (27.7 m moles) 4-(hexadecylamino)benzoic acid, 3.3 g. (36 m moles) lactic acid, 500 mg. toluenesulfonic acid and 500 ml. toluene is 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 the product separates as off-white crystals.

Workup

  1. additioncharged
  2. temperatureThe solution is refluxed for 24 hours, during which time the Soxhlet extractor
  3. additionis charged twice more with fresh sieves
  4. filtrationThe hot solution is filtered
  5. waitleft
  6. temperatureto cool, whereupon the product

Sources & evidence

ORD record
ord-b68f72fcfa234d9ebd971fa82e24e010
Source dataset
uspto-grants-1981_06
Patent number
US04272546

Reaction notes

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