Reaction #1960520

ord-d6290d8937564b92880a5d2920cac31c

Reaction equation

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

Reactants

COc1ccc2cc([C@H](C)C(=O)O)ccc2c1
Naproxen

Reagents

None

Solvents

Br
HBr

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturewas refluxed for 10 hours
  2. 2
    workup.ADDITIONIt was poured onto ice water (3000 ml)
  3. 3
    FiltrationCrude 2-(6-Hydroxy-naphthalen-2-yl)-propionic acid was filtered
  4. 4
    Otherdried
  5. 5
    Otherrecrystallized from a mixture of ethyl acetate and hexane

Procedure

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

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08303978B2uspto-grants-2012_11