which me to be: identical ith Haivente and Blanc’ $1) dinydrocamphoceénic 
acid ( (V). : ‘The acid is stable towards potassium permanganate; b. p. 138 to 139° (10 mm. Me 
‘4 amide, m.p. 169°. For sake of comparison with this acid CoHisOo, the author prepared, © a 
from > cyclopentanone, cyclopentane isobutyric acid (VI), by, reducing Wallach’s’”) ethyl Be % 
suggpevions isobutyrate in alcoholic Sony with hydragen and colloidal palladium teh 
Pee Cie ee a De aoe: 
Re oN Oreateev inn = \C{(CHa)s Be gee Oe el ke settee -C (CEs): Soh 
<t Boe ‘4 Ay sat 3 ; : } ; : | } or 
: A gC | pedi a(S an aaa | yet. CO , ele 
Hes} COR) CORT a) Ste ec Riding ee, ie 
—) Hydroxycamphenilanic acid Acatapnenylic a0) z - (I) Carbocamphenilonone. i gpa 
tera: - 2H, RH ACH) COMM cle ony a 
: CH (COvH)- bbe Co ee Raspes ne CH(CO.H): CH, Sr gaa | oe 
- te (III) Aa Hee acid. fhe ¢ Acid. Collide from eanpiens camphoric acid : oy 
: CH - CH. CH. CH (cris. ree Sree oan .CO.H 3 | on 
a tide | : i elhnke ‘ : Pate : ‘ Wi, 
a ~ CH(CO2H)- CH, Se aaa oles «FE Chg chia) a 
i -(V) Dihydrocamphoceénic acid. t (VI) G yelopentane isobutyric. acid. aot 
i : “i ate fw. sae" ERG ane : a er 
3 Pe at ed Coen Sawant c cH | ae 
2 Pe er CP CUCHLL COL ee HL, ~ C(CHa)s oh ae 
CH=CH eee) sco. 
. VII) © tene isobutyric acid. Sa aes es 
: | ( }) yetopen ene is - yric aci oe CO.H 
(VIII) Camphenilone~-carboxylic acid. be 
; and saponifying the resulting: saturated ester with sodium erates ‘Amide oF the | ie 
saturated acid, m.p. 141 to 142°, amide of cyclopentene tsobutyric acid, m.p. 136 to 137°. 
: The formation of cyclopentene eatoiee sae acid (VII) in the degradation of camphenic acid 
is quite possible. 
The acid CiktsO; was proved to he a. ketonic acid, in. harmony with Aeehanie 
_ assumption; it yields a phenylhydrazone (m. p. 142 to 143°) and passes over, on careful 
heating with caustic potash or on boiling with sodium methoxide or ethoxide, into 
_cis-d,l-camphenic acid. It must be regarded, therefore, as camphenilone carboxylic 
acid (VIII) and is, in all ie se te Lee aaa with Houben and Willfroth’s 3) camphenilone 
_ carboxylic acid. . 
Hintikka investigated, Deena, the behaviour of several salts of Ccamphenic — 
acid on dry distillation. Whilst the lead salt yields eee as was demonstrated 
; “y, Compt. rend. 146 (1908), 233; 147 (1908), 1314; Report April 1908, 191. — ?) Liebig’s Annalen 358 : 
(1907), sgt Report October 1907, 177. — *) Berl. Berichte 46 (1913), 2283; Report October 1918, 150. 
