Reacción #2490309

ord-2968d08bd1cc41e0b2159cacf69410b1

Ecuación de reacción

CCCCCCCCCC[N+](C)(C)CCCCCCCCCC.[Cl-]
didecyldimethylammonium chloride
COc1ccc2cc([C@H](C)C(=O)[O-])ccc2c1.[Na+]
naproxen sodium salt
→
CCCCCCCCCC[N+](C)(C)CCCCCCCCCC.COc1ccc2cc([C@H](C)C(=O)[O-])ccc2c1
didecyldimethylammonium (S)-6-methoxy-α-methyl-2-naphthaleneacetate
Rendimiento 95.0%

Reactantes

CCCCCCCCCC[N+](C)(C)CCCCCCCCCC.[Cl-]
didecyldimethylammonium chloride
COc1ccc2cc([C@H](C)C(=O)[O-])ccc2c1.[Na+]
naproxen sodium salt

Reactivos

Ninguno

Disolventes

O
water

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    ExtracciónThe product was extracted by ethyl acetate and organic phase
  2. 2
    Otrowas separated
  3. 3
    Lavadowashed with distilled water
  4. 4
    OtroEthyl acetate phase was removed
  5. 5
    Otrosolvent evaporated

Procedimiento

The stoichiometric mixture (0.025 mol) of didecyldimethylammonium chloride and naproxen sodium salt were dissolved in distilled water and stirred at room temperature for 1 h. The product was extracted by ethyl acetate and organic phase was separated and then washed with distilled water. Ethyl acetate phase was removed and solvent evaporated. The product, didecyldimethylammonium (S)-6-methoxy-α-methyl-2-naphthaleneacetate (95% yield), was dried under vacuum. The product is soluble in chloroform, acetone, and DMSO. It lacks miscibility with water and hexane. Thermogravimetric analysis: Tonset5%=156° C., and Tonset=190° C. 1H and 13C NMR (DMSO) were obtained.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08802596B2uspto-grants-2014_08