OF ARTS AND SCIENCES. 191 



of some time a crystalline precipitate of metliylfurfuramide. This 

 substance crystallizes in slender radiating needles, dissolves read- 

 ily in alcohol, ether, chloroform, benzol, or carbonic disulphide, 

 but is more sparingly soluble in ligroin. Tbe substance recrys- 

 tallized from ligroin was found to melt at 86-87°, and contained 

 the proper percentage of nitrogen. 



0.3510 grm. substance gave 27.8 c.c. of moist nitrogen at 22° and 

 under a pressure of 759 mm. 



Calculated for C 18 H 18 N,0 3 Found. 



N 9.03 8.96 



GUAIACOL. 



The larger fractions of the oil boiling above methylfurfurol were 

 those which were collected between 200° and 220°, but even after 

 long continued distillation no substances of constant boiling point 

 could be isolated. While the oil did not appear to contain an alde- 

 hyde in sensible quantities, a large portion of it was soluble in 

 aqueous alkalies, and we thought it advisable to take advantage of 

 this fact in order to simplify our task. The fractions 200-215° 

 were therefore united, shaken with a solution of sodic hydrate, and 

 the aqueous emulsion distilled with steam as long as oil passed 

 over. The alkaline solution was then acidified and again distilled 

 with steam. The neutral oil when dried with calcic chloride dis- 

 tilled at 210-220°, and we have not yet examined it further. The 

 oil which was soluble in the alkaline solution boiled between 200° 

 and 205°, and the thermometer remained for a long time constant 

 at 202°. The physical properties of this oil and the emerald-green 

 color which ferric chloride developed in its alcoholic solution left 

 no doubt in our minds that it was guaiacol, and we thought that it 

 could possibly be most conveniently identified with precision by 

 converting it into the tribromguaiacol of Tiemann and Koppe.* 

 On adding bromine to an alcoholic solution according to their 

 directions, however, we obtained an unsatisfactory product. The 

 melting point, although somewhat higher than that given by Tie- 

 mann and Koppe (102°), was not sharp, and was little improved 

 by repeated recrystallization. As the inherent disadvantages in 

 adding bromine to an alcoholic solution were sufficiently obvious, 

 we substituted glacial acetic acid for the alcohol, and at once 



* Berichte der deutsch. chem. Gesellsch., XIV. 2017. 



