2-Toluene-sulphonyloxy-3-phenoxy-hydratropic acid → Fenoprofen
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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.