ie REPORT OF SCHIMMEL 8 Co. APRIL 
b. p. 204° (748 cy d° 0.8562; pmo 1.4360. The oxide i ae colourless, 
the smell of which Socaie that of lemon oil. Sor} 
through the action of sodium amide on menthone, dissolved in ether, ammonia and 
the sodium derivative of menthone result and that the latter may be converted into _ 
alkyl menthones by the aid of alkyl iodides. The reduction of the menthone homo- — 4 
logues, obtained in this way, has now been described by E. Boedtker?); it easily takes 
place when the ketones in moist ether are treated with sodium. The formation of the ~~ 
alkyl menthones does not always run smoothly and is specially unsatisfactory if high- 3 
molecular alkyl groups are introduced. The yield depends upon the quality of the 
sodium amide; besides, the alkyl halogenide partly interchanges with the sodium amide, 
when the alkyl menthone acts as solvent. This by-reaction cannot be prevented in 
any way. From 100 g. of levorotatory menthone and 100-g. of zsopropyl iodide, only a 
few drops of the supposed-to-be isopropylmenthone were obtained; b. p. about 130° at 
20mm. About 10 g. of m-propylmenthone formed from 50 g. of menthone and n-propyl - 
bromide. The yield of isobutylmenthone was about 15 g., that of isoamylmenthone 
(b. p. 135 to 140° at 11 mm.; npa0 1.4619) about 10 g. from 50 g. of menthone. Methyl- 
menthone (b. p. 105° at 17 mm.; dpo 1.4610) and ethylmenthone (b. p. 110° at 12 mm.; 
Np»10 1.4646) were obtained in fairly satisfactory quantities. Boedtker obtained benzyl- _ 
menthone from benzyl chloride and menthone; b. p. 177° (8 mm.,); d= 0.9979; 
[a]pe3:0 + 23° 4; Npiso 1.5232. The properties of the menthol homologues, obtained by 
reduction of the alkyl menthones, and their esters are shown in the following tables: —_ 
Alkyl menthols and esters. 
B. p. d= Optical rotation - Npz00 
Methylmenthol . . . . 129 to 130° (32 mm.) 0.9124 [@]p210—2°26’ 1.4692 
Methylmenthyl acetate . 125° (17 mm.) 0.9313  [a]p20—18°7’ 1.4578 
Ethylmenthol .... . 124© (13 mm.) 0.9246 [a]pno-+4°55' 1.4769 
Ethylmenthyl acetate. . 131 to 132° (14 mm.) 0.9366 [@]pro—6°6' 1.4636 
m-Propylmenthol. . . . 141 to 145° (27 mm.) 0.9075  [@]p20 + 29°97" 1.4675 
n-Propylmenthyl acetate 152° (30 mm.) 0.9515 [@]p20—8°58' 1.4741 (199). si 
Isoamylmenthol . . . . 150° (23 mm.) 0.8985  [@]p20 + 33944" 1.4661 
Benzylmenthol*). . . . 203 to 205° (24 mm.) d=>0.9819  [a]p0 ~ 43919’ 1.5257 
Action of esters on magnesium alkyl iodides. On repeating former experiments, 
G. Stadnikow*) found that, at room temperature, the action of magnesium benzhydryl~ _ 
iodide on ethyl acetate consists only in that ethyl is replaced by benzhydryl. In the 
heat, however, benzhydrol ether is formed. By heating magnesium menthyl iodide in ~ 
absolute ether with ethyl acetate, menthyl acetate results (b. p. 113° at 19 mm). Tf 
ethyl propionate is used, menthyl propionate (b. p. 122 to 123° at 18mm.) forms ina ~~ 
similar way. Menthyl benzoate is obtained by heating 0.2 molecule of magnesium 
menthyl iodide in absolute ether with 30 g. of ethyl benzoate; m. p. 54.5 to 55°, b. p. He a 
to 192° at 18 mm. Through the action of ethyl acetate on the magnesium pees e | 
iodide, a hydrocarbon of the formula CioHisg is obtained (b. p. 182 to 184° at hy. ) Ls 
1) Compt. rend. 188 (1904), 1139; Report October 1904, 125. — *) Bull. Soc. chim. IV. 17 (1915), 360. 
%) See Wallach, Liebigs Annalen 805 (1899), 263. — F. W. Semmler, Berl. Berichte 37 skecag 236. — te 
russ. phys. chem. Ges. 47 (1915), 1113; Chem. Zentralbl. 1916, I. 1067. at 
