P ienene 1 enzene) by soneactine nydreeer: : a pt ees 
solution of 3.9 &. of phenylethy! acetate, 30 cc. of glacial aceti 
‘ avabic solution. It is a eoroutless liquid ae an 7 oeece ie Seely recal it 
ee of roses, and boils between 206 and 209°. The oxidation of this alcohol v 
| epi yield, on hydrogenation, the same Heinys the new iy 
methyl-2-(hydroxy-3'-butyl)-hexahydrobenzene. For this purpose, 10 g. of @- or @-i | 
‘were dissolved in 950 cc. of glacial acetic acid, when 10 cc. of a 5 per cent. chic 
absorption took place very quickly. The two first molecules w re. 
j : absorbed within 40 minutes, the third three hours later.. From 
C _ liquid, a body melting between 142 and 143 
Pee rea cet (20 mm.) (doo 0.9126) was isolated, the hexahydro- % 
| OH ionone. It smells of cedar wood and forms an — 
sla deeaeas CH; acetate boiling at 131° (11 mm.). Be it here recalled a : 
CH, that Skita obtained, some time ago‘), dihydroionone and tetra- 
hydroionone through hydrogenation of e@- and 8-ionones i 
palladous chloride and hydrogen. -_ 
5 9. of pulegone, dissolved in 40 cc. of glacial acetic acid, were mixed with 10 ce. eT 
of a 5 per’cent. solution of chloroplatinic acid, 15 cc. of colloidal platinum and 20 tc 
of a 2 per cent. gum arabic solution, when under a pressure of 2 atmospheres the first 
molecule of hydrogen was absorbed after 10 minutes, the second after a further | 
20 minutes. The liquid then yielded menthol, b.p. 207 to 209°. With an equal con- 
centration of the platinum, it was possible to convert pulegone into menthol likewise ae 
in an aqueous-alcoholic solution, when the two molecules of hydrogen were taken up ee 
within 60 minutes. On a previous occasion, Skita and H. Ritter?) had obtained menthone 
on reducing pulegone by means of colloidal platinum and hydrogen, whereas menthol — 
was then formed merely as a by-product. They also reduced, at the time, phenylacet- 
aldehyde to phenylethyl alcohol, with the aid of palladium and hydrogen at a Presser é 
of 6 atmospheres. a a 
Hexahydroionone. 
Preparation of ethers from aldehyde or ketone acetals.. By the reaction of organo- 4 
magnesium compounds on aldehyde and ketone acetals, A. E. Tschitschibabin and — 
s S. A. Jelgasin®) obtained, in addition to compounds already known, some ethers — 
distinguished by a characteristic odour. The best yield of ethers was obtained in 
“ most cases when organo-magnesium compounds permanently reacted on a considerable 
pss excess of acetals. Such conditions are best secured by adding an ethereal solution of — 
organo- magnesium compounds to the acetal, which is being kept at a temperature | 
which the reaction takes place easily. In a number of experiments with methyla 
benzyl-magnesium chloride, carried out by boiling under a reflux condenser 
:; as by heating in a sealed tube at various temperatures, the following produc 
formed: toluene, eae phenylethyl alcohol (b. p. 212°) or its isomeride a 
a 1) Berl. Berichte 45 (1912), 3312; Report April 1918, 143. — 2) Berl. Bene 43. (910, 393 
4 April 1911, 186. — 8) Berl. Berichte 47 (1914), 1843. Consult also ibidem 48. Sera 
a 
a 
