186 PROCEEDINGS OF THE AMERICAN ACADEMY 



XIII. 



CONTRIBUTIONS FROM THE CHEMICAL LABORATORY 

 OF HARVARD COLLEGE. 



OX CERTAIN PRODUCTS OF THE DRY DISTILLATION 



OF WOOD: METHYLFURFUROL AND METHYL- 



PYROMUCIC ACID.* 



By Henry B. Hill and Walter L. Jennings. 



Presented November 9, 1892. 



Several years ago, one of us described f the occurrence of fur- 

 furol in not inconsiderable quantity among the products of the dry 

 distillation of wood at low and carefully regulated temperatures, as 

 carried on at Brooklyn under the direction of Dr. E. R. Squibb. 

 Although attempts were made at the time to separate by fractional 

 distillation the higher boiling constituents of the crude furfurol, 

 ordinary boiling flasks alone were employed, and the results were 

 so far from encouraging that a more thorough investigation was 

 for the moment relinquished. The gradual accumulation of larger 

 quantities of these higher-boiling oils encouraged us to renew the 

 investigation, and we soon found that fractions of constant boiling 

 point could readily be isolated by using in the distillation the ex- 

 tremely effective bead columns of Hempel.t The most noticeable 

 fraction which we obtained was one boiling at 184-186°. This 

 proved to contain chiefly methylfurfurol, a preliminary account of 

 which was published § soon after its identification. A few months 

 later Maquenne, || and Bieler and Tollens,^ quite independently of 



* A part of the work described in the following paper was presented in the 

 form of a thesis to the Faculty of Arts and Sciences of Harvard University in 

 May, 1892, by Walter L. Jennings, then candidate for the degree of Doctor of 

 Philosophy. 



t These Proceedings, XVI. 155. 



f Zeitschrift anal. Chem., XX. 502. 



§ Berichte der deutsch. chem. Gesellsch., XXII. 607. 



|| Comptes Rendus, CIX. 571. 



1 Berichte der deutsch. chem. Gesellsch., XXII. 3062 ; Ann. Chem. u. Pharm., 

 CCLVII. 110. 



