12 
of the melting point 57°, and should therefore be designated as 
p-methoxyhydratropic aldehyde. Its formation is thus explained by 
Bougault : 
CH3O — QH^ — CH = CH — CH3 
CH3O — Cg H4 — CH(OH) — CHI— CH, 
CH3O — CgH^ — CH — CH — CH 
CHgO — CgH^ — CH< 
CHO 
'CH3. 
It forms a colour- and odourless liquid with a nauseous, burning 
taste, boils at 255° to 256°, and has the specific gravity at 15° of 
1,069. Its bisulphite compound can be crystallised from water. The 
oxime obtained in the usual manner melts at 96°. 
The acid belonging to it, or better still the bisulphite double- 
compound of the aldehyde, can by further oxidation be converted 
into the ketone 
C H3 O — — C O — C H3 (melting point 38°) 
and the acid 
CH3O — CgH^ — COOH (melting point 88° to 89°). 
Entirely analogous to anethol is the behaviour during these various 
reactions of isosafrol, methyl isoeugenol, and isoapiol. The bodies 
with allyl side-chain (such as methyl chavicol, safrol) also react in the 
same manner with iodine and mercuric chloride or mercuric oxide, 
but here the reaction is less pronounced, and an excess of mercuric 
oxide does not produce the corresponding aldehyde. A further differ- 
ence between the two classes of bodies is this, that the addition- 
products from bodies with propenyl side -chain, when treated with 
silver nitrate, produce iodide of silver, and the aldehyde belonging to 
it, whilst those from bodies with allyl side-chain form iodide of silver 
but no aldehyde. On the other hand, the addition-products from all 
the bodies referred to, are reconverted into the crude material by zinc 
and glacial acetic acid. 
The author has produced the following bodies by precisely the 
same methods as in the case of anethol : 
I. From isosafrol, methylene -3,4 -dioxyhydratropic aldehyde 
y^O^ ^CHO 
'\o/ ' ' \CH3, 
a liquid free from colour and odour. Boiling point 279° to 280°; 
d^5 = 1,203. Melting point of the oxime 71°. Melting point of 
