Reacción #74880

ord-d1dca84c9b584950b7b5fa1a15b7b248

Ecuación de reacción

CCCCCCCCCCCCCCCCCC(=O)Cl
stearic acid chloride
OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CO
sorbitol
Cl
hydrochloric acid
→
CCCCCCCCCCCCCCCCCC(=O)O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CO
sorbitol stearate

Reactantes

CCCCCCCCCCCCCCCCCC(=O)Cl
stearic acid chloride
OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CO
sorbitol
Cl
hydrochloric acid

Reactivos

Ninguno

Disolventes

Cc1ccccc1
toluene
c1ccncc1
pyridine

Condiciones de reacción

Temperatura
90°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.ADDITIONare added dropwise to this mixture over 25 minutes
  2. 2
    Otro(at approx. 110° C.)
  3. 3
    Otrofor 1 hour
  4. 4
    Temperaturaunder reflux
  5. 5
    TemperaturaAfter cooling
  6. 6
    Lavadois then washed with water until neutral and
  7. 7
    Secadodried with dehydrated sodium sulphate
  8. 8
    OtroAfter concentration of the organic phase the sorbitol stearate crystallizes
  9. 9
    OtroIt is recrystallized from methanol

Procedimiento

411.5 g (1.358 mols) stearic acid chloride are dissolved in 3 l toluene and heated to 90° C. 41.23 g (0.22 mols) of sorbitol, dissolved in 200 ml pyridine are added dropwise to this mixture over 25 minutes. The solution is boiled (at approx. 110° C.) for 1 hour under reflux. After cooling, dilute hydrochloric acid is added to acidify the mixture, which is then washed with water until neutral and dried with dehydrated sodium sulphate. After concentration of the organic phase the sorbitol stearate crystallizes. It is recrystallized from methanol.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04174325uspto-grants-1979_11