Toluene → Diclofenac
Reaction equation
C1(C)C=CC=CC=1.C([N:15]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][C:31]([OH:33])=[O:32])[C:16]1[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:23])C1C=CC=CC=1>ClC1C=CC=CC=1Cl>[Cl:22][C:21]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:23])[C:16]=1[NH:15][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][C:31]([OH:33])=[O:32]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
In an autoclave, 55 ml of toluene, 4 ml of o-dichlorobenzene, 10.0 g of N-benzyl-o-(2,6-dichloroanilino)phenylacetic acid and 2.0 g of 5% Pd-alumina were charged and it was purged with hydrogen gas and hydrogen gas was fed at 70° to 75° C. under a pressure of 10 to 20 cm H2O for 1.5 hours. The reaction mixture at the same temperature was filtered to remove 5% Pd-alumina and catalyst was washed with 35 ml of THF. The filtrate and the washing were combined and THF and toluene were distilled off. The residue was admixed with 200 ml of n-hexane and cooled to obtain 7.0 g of o-(2,6-dichloroanilino)phenylacetic acid as colorless crystals. Yield: 91.2%