Lactic Acid → 1-Carboxyethyl 4-(8-cyclohexyloctylamino)benzoate

HRID 903410Notes

Reaction equation

HRID 903410 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:25]([OH:30])(=[O:29])[CH:26]([CH3:28])O.C1(C)C(S(O)(=O)=O)=CC=CC=1>C1(C)C=CC=CC=1>[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([O:22][CH:26]([C:25]([OH:30])=[O:29])[CH3:28])=[O:21])=[CH:18][CH:17]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 612Lactic AcidHCID 69252-Methylbenzenesulfonic acidHCID 204757724-(8-Cyclohexyloctylamino)benzoic acid

Product 1

HCID 204757971-Carboxyethyl 4-(8-cyclohexyloctylamino)benzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A flask containing 10.0 g. 4-(8-cyclohexyloctylamino)benzoic acid, 3.3 g. lactic acid, 500 mg. toluenesulfonic acid and 500 ml. toluene is equipped with a Soxhlet extractor charged with activated 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. 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 the product

Sources & evidence

ORD record
ord-3e433929930747c194e1de5e9821be01
Source dataset
uspto-grants-1980_10
Patent number
US04227014

Reaction notes

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