276 REPORTS ON THE STATE OF SCIENCE. 
Cyclic ketones behave normally towards Grignard’s reagent ; thus 
Zelinsky | converted cyclopentanone 
into methyl (1)-cyclopentanol (1) 
CH, . CH, 
oH, c \ pou 
CH,.CH,“ ‘CH, 
by means of magnesium methyl iodide. As an example of the application 
to a cyclic ester, Perkin’s synthesis of terpineol,? 
CH . CH, 
cH, .c& SoH . O(CH,), . OH 
\CH, . GHZ i 
from ethyl A®.tetrahydro-p-toluate 
CH . CH 
cH, .c% 
“cH , COOC,H 
\cuH, . CH, | 
may be quoted. 
Tertiary alcohols are also obtained by other methods of less importance 
for preparative purposes. Grignard*® showed that when an ethereal 
solution of a magnesium alkyl halide is saturated with carbon dioxide, and 
the product then boiled with an excess of the reagent, trialkylcarbinols 
are obtained :— 
RMgX +CO,=R . COOMgx 
R 
R. COOMgX + 2R/MgX = we . OMgX + MgO + MgX, 
h’ 
R R 
OH 
RY C.OMgX+H,0=R4C . OH + Mgt 
zZ \x 
B’ R 
As will be pointed out Jater, a general method for making carboxylic 
avids is to pass carbon dioxide through the Grignard reagent and then 
decompose the product by water ; thus Zelinsky * describes the elegant 
method of obtaining benzoic acid by the action of carbon dioxide on 
magnesium phenyl iodide :— 
C,H,l+ Mg=C,H,Mgl 
C,H,Mgl + CO,=C,H, . COOMgI 
C,H, . COOMg1+H,0=0,H, . COOH + MglOH 
But this type of action is not always so simple. Schroeter? sub- 
stituted phenyl bromide for the iodide in the making of the Grignard 
reagent, which with carbon dioxide gave triphenylcarbinol as the main 
1 Ber., 1902, 35, 2683. 
2 Trans. Chem. Soc., 1904, 85, 654. 
5 Compt. rend., 1904, 138, 152; Bull. Soc. Chim., 1904 [3], 81, 751. 
* Ber., 1902, 35, 2692. 
s Jbid., 1903, 86, 3005. Compare Meyer and Togel, Annalen, 1906, 347, 55, 
