— 119 — 
a) M en t hone. By condensation of benzaldehyde with menthone 
in alkaline solution, he obtained a product of the boiling point 193° 
(15 mm) the specific gravity 1,0145, and the index of refraction 1,549. 
He allowed hydroxylamine to act on this benzylidene menthone and 
obtained a hydroxylamine addition-product (melting point 162°) which 
is soluble in acids, and is again precipitated by alkalis. From this 
is formed by reduction dihydrobenzylidene mentholamine. If the 
crude material had been an oxime, the reduction-product would no 
longer have contained oxygen. Semmler has drawn up the following 
constitutional formulae for these bodies: 
CH. CH. 
CH 
CH 
H„C 
C = CH . CgHg 
CO 
HgC 
H,C 
CH 
CO 
CH(NH . OH)C6H5 
CH 
i 
CH 
CH 
I 
CH 
CH3 CH3 
Benzylidene menthone 
H,C 
CH3 CH3 
Benzylidene menthone hydroxylamine. 
CH3 
i 
CH 
CH — CH(NH2)C6H5 
CH . OH 
CH 
I 
CH 
CH3 CH3 
Dihydrobenzylidene mentholamine. 
Benzylidene menthone can be reduced to dihydrobenzylidene menthol, 
and the latter can then be oxidised into dihydrobenzylidene menthone. 
b) Camphorphorone. If camphorphorone is reduced with sodium 
and alcohol, dihydrocamphoryl alcohol is formed. Boiling point 185° 
to 192°, d2oo=o,899; aj3= 1,4604. Semmler expresses the constitution 
of this body by the following formula: 
CHo. /CH.OHv 
CH — CH 
CH — CH, 
CH. 
CH„ 
CH, 
