302 



PROCEEDINGS OF THE AMERICAN ACADEMY 



p-Dlchlorbenzo-p-difurfuran a-dlmethyl ^-dicarhoxylic Ether, 



CI O 



HjCoOoC 



H,C 



CH, 



CO2C2H5. 



O 



CI 



The above hydroquinone, when boiled for about an hour in acetic 

 acid solution containing a few drops of concentrated sulphuric acid, is 

 converted quantitatively into a benzodifurfuran derivative, which, since 

 it is insoluble in alkalies, can easily be separated from the original 

 substance. After precipitating by addition of water and treating with 

 dilute sodlc hydrate, the substance is crystallized from acetic acid 

 (95%) and obtained in long transparent prisms melting at 175°. 



0.2006 gram substance dried at 120° gave 0.3965 gram CO2 and 



0.0748 gram H2O. 

 0.2647 gram substance dried at 120° gave 0.1886 gram AgCl (Carius). 



The fiirfuran compound is unquestionably formed according to the 

 following equation : — 



CI 



CO,C,H,-C 



CH,-C-OH HO- 



OH HO-C-CH, 



-C CO2C2HS 



CI 



p-Diohlorhydroquinonediacetoacetic Ether. 



CI o 



C00COH5 



CH3 



CH, 



CO2C2H5 



+ 2H2O 



O CI 



^-Dichlorbenzo-^-difurfuran o-dimethyl j3-dicarboxyIic Ether. 



