3-Chloro-4-(2-chloro-3,6-dimethyl-4-nitrophenoxy)-1,1'-biphenyl → 4-(2-Chloro-4-phenylphenoxy)-2,5-dimethyl-3-chloroaniline
Reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([N+:12]([O-])=O)=[C:7]([CH3:15])[C:6]=1[Cl:16]>[Pt].C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([NH2:12])=[C:7]([CH3:15])[C:6]=1[Cl:16]Participants
4
Procedure
A 500 milliliter rocking Parr hydrogenator was charged with a solution of 13.5 grams (0.035 moles) of 4-(2-chloro-4-phenylphenoxy)-2,5-dimethyl-3-chloro-nitrobenzene prepared in Part A and 135 milliliters of toluene. To this solution was added 1.0 gram of a catalyst of 5% platinum on carbon and the reactor was sealed. The reactor was purged twice with nitrogen and then twice with hydrogen. Hydrogen was then introduced to a pressure of 31 psi and this pressure was maintained until the hydrogen up-take ceased, i.e., about 1.5 hours. The material was removed from the rector, filtered and concentrated (toluene removed under vacuum) to give a viscous oil. Crystallization from a hexane-ethyl acetate mixture afforded 10.6 grams of a tan powder having a melting point of 117° C.-119° C. Elemental analysis of the tan powder indicated the following: