2 ART. 4. Y. SHTBATA : THE ACTION OF 



of plithalide being produced instead of the expected glycols. The 

 reaction is to be formulated as follows : 



/COOE /CR'R'.OMgX /OR's. 



C,h/ +2R'MgX >CcH,< — ^CcH/ >0 



\COOR \COOR \C0 / 



Generally, however, the reaction goes one step further, the 

 ketone group contained in the dialkyl plithalide, formed as above, 

 combining with another molecule of the Grignard reagent and 

 the resulting compound decomposing in contact with water 

 and producing the anhydro-compound, as shown below'^ : 



/CR\ H2O /CR'o — . 



C,h/ >0 + R'MgX >C,E/ >0 > 



\C0 / \CR'(OH)/ 



/OR 9 — y 



c„h/ >o+h..o 



The compound is to be called l:l-dialkyl(aryl)-3-alkylene 

 (arylene)-phthalane, because it may be considered as a derivative 



of CgH4<^ )iO, which has been recently named " Phthalan " 



by A. Ludwig."^ The intermediate substance — carbinol — could not, 

 however, be isolated. 



This difference in the action of the Grignard reagent on the 

 esters of succinic and 0-phthalic acids which, from the study of 

 their derivatives, are regarded as j)erfectly analogous one to the 

 other, may, however, be easily explained by taking into con- 

 sideration the position of the carboxyl groups in the molecule 

 of the two acids. 



1) It appears likely that the dehydration is due to tlie action of the excess of the 

 Grignnrd reagent employed. Compare F. W. Kay and W. 11. Perkin, jun., Jonrn. Chem. 

 Soc., (1900), 89, 848. 



2) Ber., (1907), 40, 3062, 



