147 — 



/?-Fencholenic acid lactone (b. p. 116 to Ii8° [8 mm. pressure]; 

 m. p. 68 to 69 ; d25o 1,0343; n D 1,46757 [cooled below the solidifying 

 point!]), when treated with sodium and alcohol, passes over in the 

 corresponding glycol of the b. p. 142 to 143 (8 to 9 mm. pressure), 

 which also yields an oxide : — 



CH 



H C 



H„C 



C(CH 3 ) 2 H 2 C 



CO 



H C 



CH 



CK 



CH 



C(OH)(CH 3 ) 2 H 2 C 



XH - OH 



H 9 C 



C(CH 8 ) 2 



CH 



CCH 3 



oxide 



C;CH, 

 glycol 



The reduction of a <5-lactone (coumarin) yielded, besides a-hydroxy- 

 dihydrocinnamic acid, a hitherto unknown phenol alcohol, o-hydroxy- 

 dihydrocinnamic alcohol C 9 H 12 2 (b. p. 177 to 17 8° [8 mm. pressure]; 

 d2o° 1,1293; n D 1,55984), of which Semmler produced in quantitative 

 yield the corresponding oxide, chromane. The alcohol yields with 

 benzoyl chloride a benzoyl compound of the m. p. 99 to ioo°. 



CH 



CH 



HC 

 HC 



C.CH:CH . CO 



^O "" 



HC 

 HC 



CH 

 coumarin 



CH 



C.CH 2 .CH 2 . CH..OH 

 COH 



phenol alcohol 



CH 



CH 



HC 



HC 



CH 2 



CH, 



CH o 

 chromane 

 When reducing the 8-lactone of 2,6-dimethyl-octane-3-ol acid from 

 menthene, Semmler obtained a glycol C 10 H 22 O 2 , b. p. 14 7° 

 (10 mm. pressure); the conversion is as follows: — 



CH(CH 3 ) 2 



CH(OH) 



CKOH 





CH(CH 3 ), 



H^C 



CH 



— 



/ 



CO 



S 



CH 

 -lactorj 



CH 2 



•CH £ 

 e 



H 2 C 

 H 2 C 



CH, 



CH • CH 3 

 dimethyl- 2, 6-octanediol»3, 8 

 10* 



