JACKSON AND GRINDLEY. — ACETALS FROM QUIN0NE8. 455 



case for one gram of quinone is 0.213 gram, and the observed results 

 come as near to this number as could be expected, when the roughness 

 of the method is considered. This conclusion is confirmed by ilie 

 yield of the salt obtained from 3 grams of quinone, which vva.> 4.7 

 grams, whereas, if only one molecule of sodic ethylate had been ;ui<ied 

 to each molecule of the quinone, the yield should have been 4.9 grams. 

 The study of other parts of this research has occupied our tiim- so 

 completely that we have been unable to do more on this division of 

 the subject, but we hope that this work can be taken up again in tliis 

 Laboratory at an early date. 



Experiments on Phenoquinone. 



It has been suggested in the introduction that phenoquinone and 

 quinhydrone may be hemiacetals similar to those studied in this paper. 

 In that case phenoquinone should contain two hydroxyl groups, and 

 form salts. Accordingly, we have tried to obtain a salt of it, although 

 the chances of success were not great as Wichelhaus * has stated that 

 phenoquinone forms no salts, but is decomposed by alkalies. Still we 

 thought that possibly by using sodic ethylate in insufficient quantity 

 we might succeed, as the replacement of the hydrojjen by the metal 

 might take place in preference to the decomposition of the pheno- 

 quinone, especially as Wichelhaus also states that it gives a blue color 

 with alkalies. "We proceeded as follows. One gram of phenoqui- 

 none t was dissolved in ether, and treated with an alcoholic solution 

 of the sodic ethylate made from 0.1 gram of sodium; as 0.1 o4 ofram 

 of sodium would be required for two atoms of sodium to each mole- 

 cule of phenoquinone, there was a considerable excess of this latter 

 substance. As soon as the sodic ethylate was added, a heavy fioccu- 

 lent dark green precipitate was formed, which was filtered out, washed 

 thoroughly with ether, and dried over sulphuric acid and paraffiiip. We 

 hoped at first that this was the salt of phenoquinone, and three sodium 

 determinations seemed to confirm this idea, as they gave 13.14, 13,41, 

 and 14.31 per cent of sodium, which is not far from the > iimlier 

 calculated for a sodium salt of phenoquinone, since that is 13.52 per 



* Ber. d. ch. G., V. 248. 



t The phenoquinone was made by adding one equivalent of quinone dissolved 

 in hot ligroine to two equivalents of phenol dissolved in a small quantity of the 

 same solvent. The mixed solutions were wanned for a few minutes, and then 

 on cooling beautiful red crystals separated, which were purified by recrystalli- 

 zation from alcohol. 



