NEW PHILIPPINE ESSENTIAL OILS. 339 



from it, recalls the observations of Knoevenagel ^ in regard to the group 

 CH=CH— CO. Dimethyl cyclohexanone yields the acid, 



H,C 

 CH,-HC 



a snlphonic acid radial remaining attached to carbon. Such compounds 

 combine with two molecules of sodium acid sulpliite. 



That the substance is a ketone and not an aldehyde is indicated by 

 its behavior toward ammoniacal silver nitrate and fuchsin sulphurous 

 acid. The phenylhydrazone, described by Bacon as melting at from 

 153° to 155°, was prepared and after several crystallizations from liot 

 alcohol melted shai-ply at 161°. I have found that the ketone reacts 

 with one molecule only of phenylhydrazine, the resulting phenylhydrazone 

 having the composition CieHgoO^ : IST • NH • CgHg as shown by the follow- 

 ing analysis 



0.2057 gram substance gave 14.2 cubic centimeters nitrogen, measured at 30°, 

 and 760 millimeters. 



Calculated for CioH2„04=N ■ NH ■ CoHj pfr "c°ent. 



N=7.33 7.48 



Hanus' solution of iodine in glacial acetic acid indicates only one double 

 linking, altbough two and possibly three are present. 

 0.2035 gram substance absorbed 0.171 grain iodine. 

 Calculated for one double bond=0.176 gram iodine. 



According to Thieles' theory of partial valences, the group 

 — HC=CH — CO is very reactive. This probably is the group attacked. 



An alkaline solution of bromine, or hypobromite, gave bromoform, 

 recognized by conversion into ordinary carbylamine by the addition of 

 aniline. 



The remaining four oxygen atoms are present in two carboxyl gTOups, 

 since no evidence was adduced indicating a free hydroxyl group. 



A small sample of the substances was heated to 100° for 3 hours with acetic 

 anhydride, but the unchanged material was recovered. Acetyl chloride entirely 

 decomposes the compound, yielding- nothing but a tar. 



After several unsuccessful trials it was found that a crystalline potassium 

 salt coiild be produced on heating with an excess of a solution of caustic potash 

 in absolute alcohol. This salt crystallizes from hot absolute alcohol in minute 

 needles, often in feathery aggregates. The addition of potassium ethylate to 

 the solution in absolute alcohol increased the yield of the reerystallized salt. 

 It is exceedingly soluble in water. The lead salt, made by adding lead nitrate to 



'Ber. d. deutschen. Chem. Ges. (1904)^ 37, 4041. 



