Reaction #214122

ord-1641bf210f95403c95146351e4314664

Reaction equation

CCCCCCCCCCCCCCCCNc1ccc(C(=O)O)cc1
4-(hexadecylamino)benzoic acid
CC(O)C(=O)O
lactic acid
Cc1ccccc1S(=O)(=O)O
toluenesulfonic acid
→
CCCCCCCCCCCCCCCCNc1ccc(C(=O)OC(C)C(=O)O)cc1
1-carboxyethyl 4-(hexadecylamino)benzoate

Reactants

CCCCCCCCCCCCCCCCNc1ccc(C(=O)O)cc1
4-(hexadecylamino)benzoic acid
CC(O)C(=O)O
lactic acid
Cc1ccccc1S(=O)(=O)O
toluenesulfonic acid

Reagents

None

Solvents

Cc1ccccc1
toluene

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONA flask containing 10.0 g
  2. 2
    workup.ADDITIONcharged
  3. 3
    TemperatureThe solution is refluxed for 24 hours, during which time the Soxhlet extractor
  4. 4
    workup.ADDITIONis charged twice more with fresh sieves
  5. 5
    FiltrationThe hot solution is filtered
  6. 6
    workup.WAITleft
  7. 7
    Temperatureto cool, whereupon the product

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04254138uspto-grants-1981_03