— 146 



from the corresponding aliphatic, hydroaromatic, and aromatic lactones 

 by reducing these with sodium and alcohol. The yields fluctuate 

 between 20 and 6o°/o- The reduction of 7-valerolactone yielded, 

 besides the glycol (pentane- 1,4-diol, CH 3 • CH(OH) • CH 2 • CH 2 • 

 CH 2 • OH), the corresponding hydroxyvaleric acid, which with con- 

 centrated sulphuric acid can be reconverted in the lactone. After 

 treatment with alcoholic hydrochloric acid in a sealed tube (3 hours 

 at 150 ), the glycol yielded ^-pentylene oxide 



CH3.CH .CH 2 .CH 2 .CH 2 . 



I o 1 



Wallach's pulegenic acid lactone gave, in a yield of about 4o°/ , 

 the glycol C 10 H 20 2 x ) (b.p. 137 to 140 [10 mm. pressure]; d 2 o° 0,9945; 

 n D20° I >47 1 5)> which could be converted by alcoholic hydrochloric or 

 sulphuric acid in an oxide C 10 H 18 O, and which may possibly be 

 a y- oder ^-glycol of the following constitution : — 



H Q Cs 



H,0 



CH.CH 2 - OH 

 y CH- CK 



>C(OH) — CH< 



H0.H o Cv 



H Q C- 



CH.CH 2 .OH 

 z CH • CH, 



>CH— CH< 



CH CH, 



CH 2 CH 2 



The glycol of a-fencholenic acid lactone (m. p. 77 to 7 8°), which 

 latter was designated by Cockburn 2 ) as a-fencholenic acid, but which 

 Semmler has now identified as a lactone by conversion in an acid 

 C 10 H 18 3 by means of alkalis, boils at 158 to 161 (11 mm. pressure), 

 and melts at 59 to 6o°. Boiling with dilute sulphuric acid produces 

 in a yield of 6o°/ , an oxide C 10 H 18 O (d2o° 0,918; n D 1,46012), 

 which Semmler considers identical with Wallach's 3 ) fenchenol from 

 fencholenic alcohol. The following graphic formulae explain the con- 

 version from lactone to oxide: — 



CH 



C(CH 3 ) 2 



H 2 C 

 H C 



CH 



CH, 



C(CH 3 ) 2 



CH,.OH 



H 2 C 

 H C 



CH 



CH, 



C(CH 3 ) 2 



C -OH 

 CH 3 

 glycol 



C 

 CH 3 

 oxide (fenchenol) 



CH 2 



I 

 O 



*) Berl. Berichte 38 (1905), 146; Report April 1905, 114. 



2 ) Journ. chem. Soc. 75 (1899), 506. 



3 ) Liebig's Annalen 284 (1894), 338; 300 (1898), 321. 



