Heys Peer tae AES pe aah ESAS eee, « i 
ges Teue me Dh bars NF 
from bisulphite solution by neutralization and shaking with shee: In this. manner, 
found the following composition: — eet B 1 RO Sie ae 
ONIgitlals > Ske ae Aosests, A453 grs. RT A eae 
non-aldehydes’.. |... -about 50 grs. “about 80 ofS). ge 
salicylaldehyde. . . 0,985 grs. 1,110° orsh oe Sas a 
other aldehydes . . 3,850 ors. 4,860 grs. 0. Ea es” 
cinnamaldehyde . . not recovered. 
The aldehydes recovered smelled strongly of benzaldehyde. They dissolved in 1 
bisulphite solution, evolving heat, but depositing very little crystalline matter. On 4 
remaining in contact with the air, an acid formed (m.p. 91 to 93°), which proved to be © 
impure benzoic acid. The oxidation of the aldehydes with potassium permanganate led 2 
to benzoic acid, which.might point to hydrocinnamaldehyde, Dodge, in consequence, | 4 
oxidized 3 grs. of the mixture of ‘aldehydes with 30 cc. of official hydrogen peroxide % 
in the presence of a few drops of ferrichloride solution, keeping the solution slightly q 
alkaline by means of soda lye. A smell of anisole was to be noticed during the process, ~ 
but no hydrocinnamic acid was to be detected. On oximation, the mixture of aldehydes i. 
yielded an oxime melting at 90°, which might be identical with hydrocinnamaldoxime ~ 
(m.p. 93 to 94°) or methylsalicylaldoxime (m.p. 92°). Dodge is of opinion that the — 
presence of methylsalicylaldehyde could be explained by the oxidation, of the methyl 
cumaraldehyde present in cassia oil: — 
ACHs OCH, ; 
otlac abies Hic x 
CH: CH-CHO CHO i. 
Methylcumaraldehyde. Methylsalicylaldéhyde. ; 
Methylsalicylaldehyde can be further oxidized to form anisole: — : 
“7 Hy, -{- O a C Hs OCH; +- CO, ; t, 
Methylsalicylaldehyde. Anisole. fit 
In order to characterize the oxime still better, Dodge transformed it into methyl-_ 
Salicylic acid through oxidation with potassium permanganate, after the conversion off 
the oxime in the nitrile and the Speech of the latter had failed to vie an acid _ 
of a determined melting point.  . a 
The oxidation with permanganate, in his opinion a new method of converting an 
oxime into the corresponding acid, seems to be applicable if the acid obtained sufficiently i 
resists the action of the potassium permanganate. 
He mixed the solution of 0.231 gram of oxime in a few drops of methyl alcohol 
ee aiah nab solution until there was no further oxidation, when he acidulated Ww 
sulphuric acid and shook with ether. The acid thus obtained being still impure, Owi 
to an oily admixture, he repeated the oxidation with potassium permanganate, did 
extract with ether, however, but allowed the acidulated liquid to stand. An ac i, t 
deposited, melting at 89°, which proved to be methyl salicylic acid. hi fe 
On further treatment. of the non- aldehyde constituents Me the oe A, a 
adulteration of the oil. 
