3-Chloro-4-(2-chloro-3,6-dimethyl-4-nitrophenoxy)-1,1'-biphenyl → 4-(2-Chloro-4-phenylphenoxy)-2,5-dimethyl-3-chloroaniline

Participants

Reaction Steps

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:

Provenance & Evidence