regard to xine rabeances. the atmospherical air jeaves it anche eae pe chenlces 
reagents have either no influence or act only on the phenolic hydroxyl group. Afte 
having blocked up the hydroxyl group, one easily arrives at the 2,3-hydroxymethoxy- 
benzoic acid (m. p. 148°), which corresponds to the aldehyde, by oxidizing the benzene- 
sulphonated aldehyde, after addition of magnesium sulphate, with a 3 per cent. solution 
of potassium permanganate. If o-vanillin is melted with potassium hydroxide, one arrives — y 
at 2,3-hydroxymethoxybenzoic acid, pyrocatechol-o-carboxylic acid and pyrocatechol, — 
according to temperature. If o-vanillin is subjected to Perkin’s reaction, the chief product 
resulting is the lactone of a 2-hydroxy-3-methoxy-é-phenylacrylic acid. 
W. Mosimann and J. Tambor*) describe further derivatives of o-vanillin. They ~ 
mention e.g. the preparation of methyl carbonato-o-vanillin (m. p. 59°) by adding methyl- — “ 
chloroformate, and then some hydrochloric acid, to a well cooled solution of o-vanillin — 4 
in soda lye. Furthermore, the preparation of o-homoveratrole, 2,3-dimethoxy-1-ethyl- a 
benzene, 2,3-dihydroxy-1-ethylbenzene, o-veratric acid, 7-hydroxycoumaranone and other 
bodies is described, which are of little interest for our special domain. ; 
Derivatives of methylvanillin. Independent of Fritsch’), B. L. Vanzetti*®) prepared 
veratril and veratroin, which are analogous. compounds as benzil and benzoin, by 
condensing methylvanillin. Like Fritsch, he found that veratroin cannot be obtained 
in a crystalline state. . 
On melting veratril with potassium hydroxide, in addition to a little veratrilic acid, — £ 
chiefly veratric acid is formed and a resin, which is most likely analogous to the 
resin formed on heating benzilic acid. : 
Ketones. 
Menthone. M. Zajcev*) reports on some derivatives of menthone. On being treated a 
with allyl iodide and zinc, l-menthone ([¢]p — 27.46°), which had beed obtained by ~ 5 
oxidizing menthol, yielded 3-allylmenthanol (b. p. 125 to 129° at 18 mm.); da 0.9058; 
[@]p —3.09°. The same alcohol resulted from d-menthone: b. p. 121 to 124° (14 mm.); 
d°> 0.9061; [«], —2.88°. The saturation of these alcohols with hydrochloric acid in 
the cold, led to the corresponding chlorides, which are transparent liquids boiling 
under reduced pressure without decomposing. Treatment of the chlorides with silver 
or nickel carbonates yields 3-allyl-4°-menthene (b. p. 214 to 217° at ordinary pressure — 
and 97 to 100° at 17 mm.); dee 0.8551; [¢]p + 45.00 and + 50.86°. On oxidation with 
potassium permanganate in neutral solution, this hydrocarbon formed a polyhydric ~ 
alcohol, acetone, acetic, isobutyric and #-methyladipic acids. 3-Allylmenthanol, on a 
being oxidized with potassium bichromate and sulphuric acid, yields acetone, acetic, - 
isobutyric and @-methyladipic acids, whereas 3-methyl- Jallylioyciahea Ss acetic 
and methyladipic acids. 
1-Methyl-3-allyl-4*-cyclohexene is obtained by converting the inactive 3-methy! : 
Bee onexanol into the corresponding chloride and treating this with carbonate ° ‘i 
1) Berl. Berichte 49 (1916), 1261. — %) Liebigs Annalen 829 (1903), 37. — *) Atte R. teak dei Li 
Roma (5), 24, Il (1915), 467; Chem. Zentralbl. 1916, 1. 1143. — +4) Journ. Russ. phys. chem. Soc. 47 (1919), 
Journ. chem. Soc. 110 (1916), 1. 267. j 
