Reacción #1960517

ord-f57fe9d12bb74b0a9ff9f90d1153d2e8

Ecuación de reacción

COc1ccc2cc([C@H](C)C(=O)O)ccc2c1
Naproxen
CC(C(=O)O)c1ccc2cc(O)ccc2c1
2-(6-hydroxy-naphthalen-2-yl)-propionic acid
Rendimiento 81.0%

Reactantes

Reactivos

Ninguno

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturawas refluxed for 10 Hours
  2. 2
    workup.ADDITIONpoured onto ice water (3000 ml)
  3. 3
    FiltraciónCrude 2-(6-hydroxy-naphthalen-2-yl)-propionic acid was filtered
  4. 4
    Otrodried
  5. 5
    Otrorecrystallised from a mixture of ethyl acetate and hexane

Procedimiento

A mixture of Naproxen (500 grams) and 48% HBr solution (1500 ml) was refluxed for 10 Hours, poured onto ice water (3000 ml), and stirred for 30 minutes. Crude 2-(6-hydroxy-naphthalen-2-yl)-propionic acid was filtered, dried and recrystallised from a mixture of ethyl acetate and hexane to give pure 2-(6-hydroxy-naphthalen-2-yl)-propionic acid (380 grams, 81%) as a white powder with a melting point of 186-188° C.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08303978B2uspto-grants-2012_11