Naproxen → Desmethylnaproxen

HRID 558027Notes

Reaction equation

HRID 558027 reaction equation
[CH3:1][C@H:2]([C:15]([OH:17])=[O:16])[C:3]1[CH:4]=[CH:5][C:6]2[CH:7]=[C:8]([O:13]C)[CH:9]=[CH:10][C:11]=2[CH:12]=1>Br>[OH:13][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[CH:12]=[C:3]([CH:2]([CH3:1])[C:15]([OH:17])=[O:16])[CH:4]=[CH:5]2

Participants

3

Reactant 1

HCID 156391Naproxen

Product 1

HCID 162920DesmethylnaproxenYield 81%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

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.

Workup

  1. temperaturewas refluxed for 10 Hours
  2. additionpoured onto ice water (3000 ml)
  3. filtrationCrude 2-(6-hydroxy-naphthalen-2-yl)-propionic acid was filtered
  4. customdried
  5. customrecrystallised from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-a21f650cd27c4cbf884f1ea3e17a07eb
Source dataset
uspto-grants-2011_11
Patent number
US08062653B2

Reaction notes

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