LAUKACE^E 139
0-1517 grm. of the substance yielded 0-1019 grm. H2O and 0-3154 grm. COv
0-1445 „ „ „ „ 17-4 cc. N at 19°, at 750 mm. pressure."
Calculated for C 10 H 16 N 2 O 3 :— Found :—
C 56-60 per cent. 56*70 per cent.
H 7-55 „ 7-51
N 13-21 „ 13-65 „
Cymene: C 10 HU.
For the identification of this body, a fraction boiling at 48°, at 4 to
5 mm. pressure, was first oxidised in the cold with dilute permanganate
solution, for the purpose of decomposing terpenes present, and the- oil
driven over with water vapour was boiled for some time with sodium
in order to remove possible oxygenated bodies. The oil, thus purifiedt
boiling at 175° to 177°, yielded on oxidation with 1 to 2 per cent, per-
manganate solution, with the application of heat, an acid of the melting-
point 154° to 156°, p-oxyisopropyl benzoic acid, whose mother liquors,
heated with concentrated hydrochloric acid, yielded propenyl benzoic
acid of the melting-point 161° to 162°, which dissolves with difficulty
in water. There was further obtained terephthalic acid, which also
occurs in the oxidation of cymene.
Benzaldehyde : C 6 H 5. CHO.
Some of the oil boiling at 168° to 171° (45° at 4 to 5 mm. pressure)
was treated with bisulphite. The aldehyde regenerated from the bi-
sulphite compound distilled at 174° to 179°, and was found to be heavier
than water. The body was identified as benzaldehyde by the phenyl-
hydrazone melting at 156°, and the semi-carbazone of the melting-point
213° to 214°.
Nonylic aldehyde: C 9 H 18 O.
In the fractions boiling above 180° (62° to 92° at 6 to 7 mm. pres-
sure), nonylic aldehyde was detected, in addition to benzaldehyde, cin-
namic aldehyde, and the aldehydes mentioned below. This body,
recently isolated from rose oil, was identified by the nonylic acid
(pelargonic acid), obtained by oxidation of the aldehyde with moist
silver oxide. Three analyses of its silver salt gave the following
figures:—
- 0-3129 grm. of the substance left 0-1271 grm. Ag.
- 0-3990 „ „ „ „ 0-1613 „ „
- 0-2524 „ „ „ „ 0-1040 „ ,,
Calculated for Found :—
C 9 H 1702 Ag:- , ->-,
- Ag 40-75 per cent. 40-62 per cent.; 40-53 per cent.; 41*20 per cent.
Hydrocinnamic aldehyde : C 6 H 5. CH 2. CH 2. CHO.
The semi-carbazone melting at 116° to 118° gave the following values
on analysis:—
- 0-1501 grm. of the substance yielded 0*0956 grm. H 2 0 and 0-3438 grm. C0 2.
- 0-1572 „ ,, „ „ 0-0954 „ „ 0'3617 ,,
Calculated for C 10 H1 3 ON 3 :— Found :—
- C 62-83 per cent. 62-56 per cent. ; 62-75 per cent.
H 6-81 „ 7*06 „ 6-74
Eepeated recrystallisation from hot ether raised the melting-point
to 126°. The semi-carbazone prepared for comparison from synthetic
hydrocinnamic aldehyde melted at 130° to 131°. Paucity of material
rendered a definite proof of the identity of the two products impossible.
