Sodium Hydroxide → Fenoprofen

HRID 1659804Notes

Reaction equation

HRID 1659804 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
  6. customThe benzene solution is evaporated
  7. dry with materialafter drying above sodium sulphate

Sources & evidence

ORD record
ord-a45ab53834294513bb8b1449249711a3
Source dataset
uspto-grants-1981_12
Patent number
US04304930

Reaction notes

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