Reaktion #214122

ord-1641bf210f95403c95146351e4314664

Reaktionsgleichung

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

Edukte

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

Reagenzien

Keine

Lösungsmittel

Cc1ccccc1
toluene

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONA flask containing 10.0 g
  2. 2
    workup.ADDITIONcharged
  3. 3
    TemperaturThe 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
    Temperaturto cool, whereupon the product

Vorschrift

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.

Quelle

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