with Mathes suishipie ae id or Ph. ‘Barbier’s and G. Léser’ s+) menthoglycol. 
ullact 3) ‘states for isopulegol hydrate the m. p. 75°), Barbier and Léser for their 
if oglycol the m. p. 81 to 81. 5°. Perhaps the body contained in the mother-liquor 
Be perice of mreeticel 
Bow normal PeAcHBn with organomagnesium halides. In this reaction, there are . 
ned not the secondary alcohols, as might be expected, but ether-like combinations 
a from two mnolecules of the carbinols by dehydration. This abnormal course 
sa ett hoxyl groups in the asaryl molecule. For this reason the authors®) expected to 
2 re at analogous ether-like compounds when starting from apiolaldehyde, a body 
: osely. related to asarylaldehyde. Here the reaction proceeded in dependance on the 
? modus procédendi, i. €., the ether-like bodies being formed not always, but also the 
normal secondary alcohols. For instance, the interaction of magnesium methyl 
io lide. with apiolaldehyde led to dimethoxy methylenedioxy phenyl methyl carbinol 
” 3O)2: (CH.O2): CoH - CH (OR) - CH;, m. p. 52°. In this reaction, the solution of 
n 1esium 1 methyl iodide in ether was gradually treated, with strong cooling, woth a 
Siyde i in benzene i is given to the. Solon of magnesium Be iodide in ether, symm. 
di- Be eicncthoxy methylenedioxy phenyl) ethyl ether [(CH3O)2:(CH2O2): CsH - CH (CHs3)]},O 
Berens a white crystalline product of the m. p. 122°. 
When apiolaldehyde, suspended in benzene, is allowed, with strong cool- 
it , to act on the theoretical amount of magnesium ethyl iodide, the result 
-is the normal secondary alcohol, dimethoxy methylenedioxy phenylethyl carbinol 
(CH;O). : (CH20.) : CsH-CH(OH)-C.H; m. p. 54°. But on treating apiolaldehyde with 
. mas enesium ethyl iodide without pools the ether-like compound, symm. di- (dimethoxy 
E sthylenedioxy phenyl) propyl ether, m. p. 112°, is formed. 
P) | From, phenyl magnesium iodide and apiolaldehyde, the normal carbinol, phenyl 
dimethoxy methylenedioxy phenyl carbinol (CH;O),: (CH2O2) : CeH-CH(OH)-CH;, white 
cry: stals, m. p. 72°, is obtained. 
ES _ For the preparation of apiolaldehyde, Fabinyi and Széki oxidize isoapiol not in 
> usual manner with chromic acid or with potassium bichromate, but with ethyl 
uitri rite ; the reaction proceeds evenly and the yield is considerably higher than when 
v vO rking according to the old method. For this purpose the authors mix a solution 
10° g. isoapiol in 50 ccm. ethyl alcohol in a flask mounted by a reflux condenser, 
h iro gh the latter with 7 ccm. freshly prepared ethyl nitrite and add quickly 4.5 ccm. 
ce entrated hydrochloric acid. Oxidation proceeds at once without application of 
the liquid begins to boil so that it is necessary to mitigate the course of the 
ion by immersing the flask in cold water. In a short time after termination 
) € reaction (during in the utmost 10. minutes) the contents of the flask solidify 
in Je thick mass of crystals. The yield of apiolaldehyde is on the average 40 to 
5 per cent. By the same manner, asarone could be oxidized to asarylaldehyde, 
ly with very good yield. ; 
+ +) Compt. rend. 124 (1897), 1308. — %) Liebig’s Annalen 360 (1908), 103. — %) Not 72°, as quoted by 
1 F Besides, Wallach only regards it as probable that his isopulegol hydrate might be identical with 
r’s and Léser’s menthoglycol; Prins, however, regards them actually as identical. — ‘) Berichte 39 
— 5) Ibidem. 50 (1917), 1335. 
