ON “SCIENTIFIC RESEARCH. en ike 487 
Bh “HC: cH (CHa rasa et PaCH, H,C-CH_  C(CH,), j A 
F 4 Ne . H. 5 
ae i ii CK ree + or ae a Nez Beets reduction —~> 
ipa “CH: t AOL, 
met cri. Save Hc CH, 
~Campholic acid chloride. ; : 1,2. 2. 3-Tetramethyl-1-acetylcyclopentane. 
i HeCsCH  C(CHi)e : 
Ro (a XA CHOW) CH; 
‘ De ee EEO 
oe pe 0K 
= | HEC We CHL 
eres - 1.2.2.3-Tetramethyl-1, &-hydroxyethyleyclopentane. 
Se C(CHs) 
4 : SE aaa HsC-CH C(CH))s 
H;sC-HC’. \C-CHs 3 i oe 
| : | and hae De: CHICH)» 
3 BS HCl SUIC-CH, Bee 
Bees a er ON 
= : CH. . | pial | Pais 
3 3 1.2.3.  S 4-Pentamethyl-f"-eycihexene, P22: 2-Trimethyl-3-isopropy!- *-cyclopentene. 
y : ; # & de | : 
aS  ozonisation. eat Ae wae 
ener eR CH.) C(CH)a° PCAC iC ACER 
Tae | ieee 
s C-CH and C(CH 
ie ‘Peg 3 CY (CHs)o 
amerces © C:COCH,:,%.)) A.ciay CH-COCH, 
£22: 3-Tetramethyl-4-acetyl- 1.2.3. 3-Tetramethyl-4-acetyl- 
A®-cyclopentene. ozonisation _ A’-cyclopentene. 
y 
H;C- CH C(CHs)2 
| \CO-CH(CH,)2_ 
Pee coon 
Ketonic acid CuHlaoOs- 
Camphyl carbinol and other reduction products of hydroxymethylene anton — By means 
ofa process patented some years ago’) it is possible to reduce hydroxymethylene 
camphor, .with sodium and alcohol, to camphyl glycol. Later on, Kétz and Schaeffer’) 
_ hydrogenated hydroxymethylene Eoiounds by means of colloid palladium or platinum | 
according to Paal’s and Skita’s directions and observed a very interesting formation 
of methyl ketones. As a by-product, there could be isolated, on reduction of hydroxy- 
methylene dihydrocarvone, a poor yield of the ketonic alcohol which was obtained as 
benzoyl! compound. With hydroxymethylene camphor, no reduction could be effected 
with hydrogen in presence of palladium or platinum. 
_ Basing on these experiments, H. Rupe, A. Akermann and H. Takagi”) succeeded in 
reducing hydroxymethylene camphor, by means of hydrogen and nickel at room temperature 
and under ordinary pressure, to the ketonic alcohol camphyl carbinol (Il). However, the 
‘teaction proceeded very slowly and the reduction was incomplete when finely-divided 
nickel powder was employed. The reduction passes off far better if a mixture of clay- 
_and-nickel powder is used. For this purpose, pieces of porous clay plates are ground 
4) Germ. Pat. 123909 — 7”) Berl. Berichte 45 (1912), 1952. — #) Helv. chim. acta 1 (1918), 452. 
