Reaction #2044996

ord-93c8020647ef427191a8e12682ac610a

Reaction equation

COc1ccc2cc([C@H](C)C(=O)O)ccc2c1
Naproxen
→
CC(C(=O)O)c1ccc2cc(O)ccc2c1
2-(6-Hydroxynaphthalen-2-yl)propionic acid

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.ADDITIONpoured onto ice water (3000 ml)
  3. 3
    FiltrationCrude 5 was filtered
  4. 4
    Otherdried (380 grams, 81%)

Procedure

A mixture of Naproxen (500 g, 2.774 mmol) and 48% HBr (1500 ml) was refluxed for 10 hours, poured onto ice water (3000 ml) and stirred for 30 minutes. Crude 5 was filtered, dried (380 grams, 81%) and used as such for next stage.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08409559B2uspto-grants-2013_04