128 REPORT OF SCHIMMEL & Co. APRIL 1914. 
For example, the author mixed together 10 grams pure benzaldehyde, 10,6 grams 
acetic anhydride (1 mol.-+10p.c.) and 0,1 gram contact-substance. The temperature 
was prevented from rising above 70° by cooling with cold water. After 24 hours the 
mixture was washed with water and soda-solution, after which the reaction-mixture 
generally solidified. The benzylidene diacetate obtained by this method had b. p. 154° 
(20 mm.); m. p. 46°. With copper sulphate and chloride of zinc an almost quantitative 
yield was afforded. Benzylidene diacetate can also be prepared quantitatively without 
excess of acetic anhydride with sulphuric acid or ferric chloride if the reaction is 
prepared in a freezing mixture. In that case the entire mass solidifies at room- 
temperature after some time. Cinnamic aldehyde afforded cinnamylidene diacetate 
(m.p. 85°). In this case ferric chloride and zinc sulphate were an almost complete 
failure. Vanillin yielded vanillin-triacetate (m.p.90°). Anisaldehyde afforded anisylidene 
diacetate (m.p. 67°); piperonal (heliotropine) afforded piperonylidene diacetate (m. p. 80°). 
Salicylic aldehyde and acetic anhydride yielded in part the triacetate (m, p. 103°), in 
part the disalicylic aldehyde (m.p.129°), partly also these two substances together. 
Cineol is capable of being split up, with addition of acetic anhydride, if the 
reaction is carried out in the presence of suitable catalysts. In this case, terpin 
diacetate and terpinyl acetate result. The formation of terpinyl acetate is probably due 
to the belated splitting-off of acetic acid. The addition of acetic acid to the reaction- 
mass lowers the yield of terpinyl acetate, and when acetic acid is used by itself the 
reaction proceeds with formation of dicinene. Sulphuric acid and ferric chloride are 
specially suited for decomposing cineol. The terpinyl acetate boils at 104 to 106° 
(11 mm). The terpin diacetate distilled over at 145° (14 mm.). 
C. Neuberg’), in collaboration with H. Steenbock, reports on the formation of higher 
alcohols from aldehydes by means of yeast. They describe the conversion of valeric 
aldehyde into amyl alcohol. The authors allowed carefully purified commercial valeric 
aldehyde (a mixture of zsovaleric aldehyde and methylethyl acetaldehyde), to drip slowly 
into a mixture of cane sugar and yeast in process of fermentation. After being left 
standing for 4 to 6 days the alcohol-mixture was distilled off. After drying the mixture 
over fused sodium sulphate and copper sulphate, it was possible to isolate the amyl 
alcohol by means of a Heinzelmann bi-rectificator’), the yield being from 66,4 to 84,1 p.c. 
of the valeric aldehyde used in the experiment. Sugar and yeast by themselves afforded 
only traces of amyl alcohol. The amyl alcohol obtained from valeric aldehyde consisted, 
according to the composition of the crude material, of a mixture of isobutylcarbinol 
and /-methylethylcarbinol. When valeric aldehyde and ammonia were used, a liberal 
yield of amyl alcohol was also obtained. Without the addition of sugar the amyl alcohol 
yield amounted only to 26,1 p.c. The amyl alcohol was identified from its b. p. and 
from the preparation of the «-naphthylurethane. The latter melted at 64°. The mace- 
ration-juice of yeast also has the power of reducing valeric aldehyd to amyl alcohol. 
K. Ohta*) has likewise reduced isobutyl alcohol as well as cenanthol (n-heptylic 
aldehyde), a body which is foreign to the organisms, to the corresponding alcohols by 
means of yeast. The addition of cenanthol, however, to the fermenting sugar solution, 
greatly impedes the fermentation process, and when the cenanthol is added carelessly, 
fermentation may be arrested altogether. The ¢-naphtyl urethane of the n-heptyl alcohol 
had m.p. 97°. 
1) Biochem. Zeitschr. 62 (1913), 494; 59 (1914), 188. From a reprint kindly sent to us. — 2) Chem. — 
Zentralbl. 1918, I. 968. — *) Biochem. Zeitschr. 59 (1914), 183. From a reprint kindly sent to us. 
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