Lactic Acid → 1-Carboxyethyl 4-(15-carbomethoxypentadecylamino)benzoate

HRID 1278402Notes

Reaction equation

HRID 1278402 reaction equation
[C:1]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1)([O:3][CH3:4])=[O:2].[C:30]([OH:35])(=[O:34])[CH:31]([CH3:33])O.C1(C)C(S(O)(=O)=O)=CC=CC=1>C1(C)C=CC=CC=1>[C:1]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([O:27][CH:31]([C:30]([OH:35])=[O:34])[CH3:33])=[O:26])=[CH:28][CH:29]=1)([O:3][CH3:4])=[O:2]

Participants

5

Reactant 3

HCID 612Lactic AcidHCID 69252-Methylbenzenesulfonic acidHCID 12898273p-(15-Carbomethoxypentadecylamino)benzoic acid

Product 1

HCID 211633441-Carboxyethyl 4-(15-carbomethoxypentadecylamino)benzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A flask containing 10.0 g. 4-(15-carbomethoxypentadecylamino)benzoic acid, 3.3 g. 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 4 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. additionA flask containing 10.0 g
  2. additioncharged
  3. temperatureThe solution is refluxed for 4 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 the product

Sources & evidence

ORD record
ord-afe0204fbdfb4bae9cbeecedde01d34b
Source dataset
uspto-grants-1981_07
Patent number
US04281018

Reaction notes

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