420 PROCEEDINGS OF THE AMElilCAN ACADEMY. 



much more accessible than the tetraethylacetal ; it crystalUzes well, 

 and melts at 170°. It is a curious fact that none of the benzoyl 

 compound is formed, it" the sodium or silver salt of the hemiacetal is 

 susjjended in ether instead of alcohol, and treated with benzoyl- 

 chloride. In order to obtain this benzoyl compound, therefore, it is 

 essential to use alcohol as the diluent. The reaction with ether is 

 apparently the same as that which occurs when the free hemiacetal 

 or its sodium salt is heated to 100° with benzoylchloride, the products 

 in this case beiug dichlordiethoxyquinoue and ethyl benzoate. 



When the dichlordiethoxyquinone-dibenzoyldiethylacetal is heated 

 with sulphuric acid of specific gravity 1.44 it is converted into a 

 new substance, the analysis* of which gave numbers corresponding 

 to the formula C6Cl2(OC2H5),,(OCOCoIl5)20. This body must be 

 formed by the saponification of two ethoxy groups by the sulphuric 

 acid, whereas we should have expected that the acid would have 

 attacked rather the two benzoate groups. Our experiments have not 

 as yet given us any means of determining which pair of ethoxy groups 

 has been saponified. From the formula established by analysis we 

 should infer that, after the two ethoxy groups had been converted by 

 saponification into two hydroxyls, a molecule of water was eliminated, 

 leaving the atom of oxygen spanning the benzol ring between two 

 atoms of carbon in the para position to each other. Our substance, 

 therefore, would have some analogy to cineol, if the constitution 

 ascribed to it by Briihl f is correct. We realize fully, however, that 

 such an unusual constitution as this should not be considered estab- 

 lished without the most convincing proof, and, as at present we are 

 unable to give this, we propose it only as that which accords best 

 with the results of analysis and the method of preparation of the sub- 

 stance. We have made some attempts to prepare derivatives of this 

 substance in order to throw light on its constitution, and have found 



* As our first analytical results approached the numbers calculated for the di- 

 chlordiethoxyhydroquinone dibenzoate CgCl^lOCaHgjoiOCOCgHsJo, we thought 

 that perhaps we had in hand this substance mixed with an obstinately adhering 

 impurity, and accordingly we made it from the substituted hydroquinone in 

 order to compare it with our substance, but found that the two were not iden- 

 tical, since it melts at 215°, while the melting point of our new substance is 

 142°. The bad results from our first analyses we found afterward to be due to 

 the diflSculty in securing a complete combustion of our saponification product, 

 and, after taking special precautions to insure this, numbers were obtained 

 from very carefully purified preparations agreeing excellently with those for 

 the formula given above. 



t Ber. d. ch. G., XXI. 461. Compare also Ibid., XXVII. 810. 



