THE GRIGNARD KEAGENT ON 0-PHTHALIC ESTERS. 15 



were studied, but, in these cases, no phthalane derivatives were 

 obtained, the only definite product, which has been isolated, be- 

 ing diethyl-phthalide. 



On usual treatment, a brownish yellow oil, having a dis- 

 agreeable odour resembling that of onions, was obtained in each 

 case, but, on fractional distillation under a reduced pressure of 

 12 mm., it gave no constant boiling portion, until the tliermo- 

 meter rose to 165°, when nearly the whole of the remaining 

 portion distilled over. 



This portion, after refractionation, was analysed with the 

 following results, and it proved to consist of diethyl-phthalide : 



0.2444 g. of the substance gave 0.6754 g. of CO, and 



0.1653 g. of HoO, therefore 



C=75.37 H=7.56. 



Diethyl-phthalide, C6H4\ }0, requires 



^CO — ^ 



0=75.75 H=7.43. 



Diethyl-phthalide had likewise been already obtained by R. 

 KoTHE^^ and H. Bauer"^ ; the former got it as an oil of a boil- 

 ing point of 210-214° at 210 mm., while the latter obtained it 

 in the form of crystals melting at 54°. 



In order to further identify the above product, I prepared 

 its mono-nitro derivative, according to the method described by 

 H. Bauer. The crystals obtained had a melting point of 104° 

 and agreed, in this and other respects, with the description given 

 by Bauer of mononitro-diethyl-phthalide. 



The lower boiling portions were carefully refractionated, but 

 no definite product could be isolated. 



1) Ann. d. Chem. (1888). 248, 67. 



2) Ber., (1904), 37, 735, 



