2-Toluene-sulphonyloxy-3-phenoxy-hydratropic acid → Fenoprofen

HRID 2058549Notes

Reaction equation

HRID 2058549 reaction equation
C1(C)C(S(O[C:11]2[C:21]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:20][CH:19]=[CH:18][C:12]=2[CH:13]([CH3:17])[C:14]([OH:16])=[O:15])(=O)=O)=CC=CC=1.[H][H]>[Ni]>[O:22]([C:21]1[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=1)[CH:13]([CH3:17])[C:14]([OH:16])=[O:15])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 204498332-Toluene-sulphonyloxy-3-phenoxy-hydratropic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 3342FenoprofenYield 89%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

To a solution of 4.1 g. of 2-toluene-sulphonyloxy-3-phenoxy-hydratropic acid in 150 ml. of alcohol 24 g. of a W-6 nickel catalyst are added, and the mixture is hydrogenated at 25° C., under atmospheric pressure until a calculated amount of hydrogen is used up. The catalyst is filtered off, the filtrate is evaporated and the residue is taken up in water and acidified with a 10% aqueous hydrochloric acid solution. The separated oil is extracted with chloroform, the chloroform solution is dried over sodium sulphate and evaporated. 2.1 g. (89%) of 3-phenoxy-hydratropic acid are obtained. Melting point of the corresponding cyclohexylamine salt amounts to 151° C. to 153° C.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. extractionThe separated oil is extracted with chloroform
  4. dry with materialthe chloroform solution is dried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-dea284bf1ced481384264ab11c6d3398
Source dataset
uspto-grants-1982_03
Patent number
US04317920

Reaction notes

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