456 PROCEEDINGS OF THE AMERICAN ACADEMY. 



cent of sodium ; but the study of the ethereal filtrate from the salt 

 threw a great deal of doubt on this conclusion, since it contained a 

 large amount of phenol. We think it more probable, therefore, that 

 the sodic ethylate decomj^osed the phenoquiuone into quinone and 

 phenol, and that the green salt was then formed by the action of the 

 sodic ethylate upon the quinone, the action being the same as that 

 described in the last section. This inference is strengthened by the 

 marked resemblance in appearance between the salts obtained in these 

 two cases, and also by the study of the proi^erties of the salt made 

 from the phenoquinone, since it dissolved completely in water, forming 

 a dirty green solution, and undoubtedly suffering partial decomposi- 

 tion, as ether extracted from this solution colorless crystals of hydro- 

 quiuone recognized by their melting point of 169°. The addition of 

 an acid to this solution gave no precipitate, and upon shaking out the 

 acidified liquid with ether, nothing was extracted but hydroquinone. 

 If the substance had been the desired salt of phenoquinone, phenol 

 should have been obtained from this filtrate. Although these experi- 

 ments tell against the formation of salts of phenoquinone, we do not 

 consider them absolutely final, but the study of the action of alkalies 

 on phenoquiuone under other conditions will be continued in this 

 Laboratory during the coming college year. 



As we had not succeeded in making a salt of phenoquiuone we next 

 turned our attention to the action of sodic phenylate on quinone, as, 

 if the phenoquinone is a hemiacetal, this should act as well as free 

 phenol, whereas according to the other theories of the constitution of 

 phenoquinone, it is hard to see how there should be any action in this 

 case. Sodic phenylate was made by warming the proper amount of 

 metallic sodium with a solution of phenol in benzol until the sodium 

 had entirely disappeared. As the benzol cooled, the white crystalline 

 sodic phenylate separated abundantly, and, after filtering, any free 

 phenol was removed by washing with cold benzol. Upon adding the 

 solid sodic phenylate to a solution of quinone in absolute ether a dark 

 red crystalline substance looking like phenoquinone was formed. 

 After evaporating off the ether slowly, the residue dissolved easily in 

 water with a slight green color, and acids precipitated from this 

 aqueous solution a small amount of a dark reddish solid. The ethereal 

 solution showed a tendency to turn green round the edges during the 

 evaporation which may perhaps have been due to the action of the 

 moisture in the air. If benzol was used to dissolve the quinone in- 

 stead of ether, a pink substance was foimed, which changes to a dark 

 green body when warmed. With ligroine as the solvent, a dark green 



