— — 
The corresponding nonylenic acid boils at 143° to 147° (23 mm) 
and is oxidised by permanganate into acetone and yS-methyl glutaric 
acid (melting point 85° to 86°) which leads to the following con- 
stitution: C(CH3)2C = CH . CH2 .CH(CH3).CH2COOH, a result 
agreeing fully with the oxidation-products of pulenone. 
Some time ago already Wallach^) reported on a reaction, on 
the strength of which he succeeded in displacing the oxygen of 
saturated ketones from one position in the molecule to another. 
Wallach^) has now also solved this problem successfully with 
I -3 -methyl cyclohexanone as an example. On a previous occasion 
we have already referred to the formation of 1-2 -methyl cyclohexa- 
none^) from I -3 -methyl cyclohexanone. By reduction with sodium 
and alcohol, this unsaturated ketone is converted into the saturated 
alcohol belonging to it, 1-2 -methyl cyclohexanol , which again can 
be oxidised with chromic acid into 1-2 -methyl cyclohexanone. The 
I -2 -position of the methyl and carbonyl - groups was determined by 
oxidation of the ketone into ^-acetyl valerianic acid CH3 • CO • CHg 
• C • C Hg • C H2 • C O O H and further into normal adipic acid. 
lonone. For the purpose of separating a- and ^-ionone by 
means of their hydrosulphonic acid compounds, Chuit^) recommends 
the following method. In a warm solution of the sodium salts of 
the two isomeric acids he dissolves common salt; there occurs gradually 
a separation of the more difficultly soluble a - ionone - sodium hydro- 
sulphonate which is deposited on the bottom in the form of beautiful 
white crystals. The y8-compound remains in solution, and after recrys- 
tallisation by decomposition with alkalis, can be converted into absolutely 
pure a-ionone, which is said to have a decidedly finer odour than 
ordinary commercial ionone. According to Chuit the two pure isomers 
show a distinct difference with regard to the odour; a-ionone possesses 
a more flowery odour, and reminds more of orris, ^-ionone is said 
to reproduce the odour of the violet flower more perfectly. The 
reaction -product from pseudo-ionone can, according to Chuit, also 
be enriched by one or the other isomer, by the action of cold con- 
centrated sulphuric acid, which produces chiefly ^-ionone, or also by 
weaker acids, such as hydrochloric and phosphoric acids, at low 
^) Liebig's Annalen 324 (1902), 112. Comp. Report October 1902, 88. 
2) Liebig's Annalen 329 (1903), 368. 
^) Berliner Berichte 35 (1902), 2822. Comp. Report April 1903, 90. 
^) Rev. Gen. de Chimie; acc. Chemist and Druggist 63 (1903), 1054. 
