Sodium Hydroxide → Suprofen

HRID 258887

Reaction equation

HRID 258887 reaction equation
[CH3:1][C:2]([C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:25])[C:20]2[S:24][CH:23]=[CH:22][CH:21]=2)=[CH:15][CH:14]=1)(C(OCC)=O)[C:3]([O:5]CC)=[O:4].[OH-].[Na+]>>[C:20]1([C:19]([C:16]2[CH:17]=[CH:18][C:13]([CH:2]([CH3:1])[C:3]([OH:5])=[O:4])=[CH:14][CH:15]=2)=[O:25])[S:24][CH:23]=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 104320Diethyl methyl(4-(2-thienylcarbonyl)phenyl)malonate

Product 1

HCID 5359Suprofen

Procedure

A mixture of 30.3 parts of diethyl 2-methyl-2-[p-(2-thenoyl)phenyl]malonate and 200 parts of sodium hydroxide solution 5% is stirred and refluxed for 6 hours. The reaction mixture is allowed to cool while stirring. The whole is filtered and the aqueous phase is separated. The latter is washed with benzene, acidified with concentrated hydrochloric acid solution and stirred for 15 minutes. The product is extracted with chloroform. The extract is washed with water, dried, filtered and evaporated. The oily residue is triturated twice in petroleumether. The solid product is filtered off and crystallized twice from acetonitrile: first at -20° C and then at 0° C, yielding p-(2-thenoyl)hydratropic acid; mp. 124.3° C; also named p-(2-thenoyl)-α-methyl-phenylacetic acid.

Workup

  1. temperaturerefluxed for 6 hours
  2. temperatureto cool
  3. stirringwhile stirring
  4. filtrationThe whole is filtered
  5. customthe aqueous phase is separated
  6. washThe latter is washed with benzene
  7. stirringstirred for 15 minutes
  8. extractionThe product is extracted with chloroform
  9. washThe extract is washed with water
  10. customdried
  11. filtrationfiltered
  12. customevaporated
  13. customThe oily residue is triturated twice in petroleumether
  14. filtrationThe solid product is filtered off
  15. customcrystallized twice from acetonitrile

Sources & evidence

ORD record
ord-ae9cfe22141f46d3844b893a8b28181b
Source dataset
uspto-grants-1977_07
Patent number
US04035376

Linked notes

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