Sodium Hydroxide → Fenoprofen

HRID 1074582Notes

Reaction equation

HRID 1074582 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([C:14]([C:19]#N)(C)[C:15](N)=[O:16])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:21].[Na+]>>[O:1]([C:8]1[CH:9]=[C:10]([CH:14]([CH3:19])[C:15]([OH:16])=[O:21])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 54318094HCID 54318094, compound

Product 1

HCID 3342FenoprofenYield 98.5%

Procedure

A mixture of 106.4 g. of 2-(3-phenoxy-phenyl)-2-cyano-propionic acid amide, 200 ml. of 40% aqueous sodium hydroxide and 400 ml. of alcohol is boiled under stirring for 20 hours. The alcohol is then distilled off and the residue is diluted with 200 ml. of water. The aqueous solution is acidified to pH=1 by adding concentrated hydrochloric acid. The separating oil is extracted with 3×500 ml of benzene. The benzene solution is evaporated after drying above sodium sulphate. Thus 96 g. (98.5%) 2-(3-phenoxy-phenyl)-propionic acid are obtained; the product is suitable for the preparation of salts without further purification.

Workup

  1. additionA mixture of 106.4 g
  2. distillationThe alcohol is then distilled off
  3. additionthe residue is diluted with 200 ml
  4. additionby adding concentrated hydrochloric acid
  5. extractionThe separating oil is extracted with 3×500 ml of benzene
  6. customThe benzene solution is evaporated
  7. dry with materialafter drying above sodium sulphate

Sources & evidence

ORD record
ord-8731112bb2304fe1b5061a14a930d146
Source dataset
uspto-grants-1983_07
Patent number
US04393008

Reaction notes

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