

100 



Report of Schimmel § Co. 1921. 



HC 

 H 2 C 



CH 3 



I 



CO 



C(CH 8 ) 2 



CH 3 



I 

 CH-OH 



CH 2 COOH 



HC 

 H 2 C 



C(CH 3 ) 2 



.CH,-COO-C a H e 



CH 



(III) Pinonic acid. 



CH 3 

 CHC1 



CH 



(IV) Ethylpinolate. 

 CH 3 * 



HC 

 H 2 C 



C(CH 3 ) 2 



CH 2 COOC 2 He 



CH 

 CH 2 



CH, 



CM 



CH 2 COOC 2 H 5 



CH 



(V) Ethylchloropinolate. 



CH 3 



I 

 C 



CH 



(VI) 2-Cyano-6-methyl-2 : 6-heptadiene-5-acetic acid ethyl ester. 



CH 3 



I 

 C 



CH 

 CH 2 



.yCH, 



\ 



CH a 



COOH 



CH 2 COOH 



CH 

 CH 2 



CO 



O 

 CHCO 



CH 



(VII) Dicarboxylic acid from VI. 



CH 3 



c 



c 



I 



CH 

 CH S /X CH 3 



(VIII) Anhydride of transformed dicarboxylic acid (VII). 



CH 3 



I 

 C 



CH 

 CH 2 



CO 



CH 



CH 

 CH 



COH 

 CH 



CH 3 — CH — CH 3 



(IX) Unstable ketone passing 

 into carvacrol. 



CH 3 



I 



CH 



C 

 I 

 CH 3 — CH — CH 3 



(X) Carvacrol. 



CH 3 



I 



c 



CHCOOC 2 H 5 



CH 2 

 CH 2 



COOH 



CH(CH 3 ) 2 



CH 2 -COOH 



CH 

 CH 2 



CH 



C(CH 3 ) 2 



CH 



CH 2 COOC 2 H 5 



(XI) a-Methyl-/5'-isopropylpimelic acid. 



(XII) Glycide ester from pinonic acid ester. 



