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

HRID 905271Notes

Reaction equation

HRID 905271 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 Å 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 with activated Å Linde molecular sieves
  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-36db597ef41845eea10172265d3c8478
Source dataset
uspto-grants-1983_12
Patent number
US04423051

Reaction notes

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