RECENT WORK ON THE MORPHINE GROUP 299 



This synthesis was conducted on the same lines as that of 

 morphol (cf. p. 289), the initial materials being vic.o-nhro- 

 vanillin-methylether and p-methoxyphenylacetic acid, and the 

 final product thebaol-methylether : 



CH3O 



Thebaol itself was synthesised in a similar manner, vic.o- 

 nitrovanillin being used instead of the corresponding methyl 

 ether (see p. 290). 



When thebaine hydrochloride is heated for some time with 

 dilute hydrochloric acid, a secondary base thebenine is formed, 

 whilst if concentrated acid be used a tertiary base morpho- 

 thebaine results. Under precisely similar conditions, codeinone 

 can be made to yield the same products, and there must 

 therefore be a very close relationship between the two 

 bodies — a conclusion which is further substantiated by the 

 fact that on treatment with acetic anhydride, the nitrogen-free 

 product from thebaine — thebaol — is the monomethyl ether of 

 that resulting from the action of the same reagent on codeinone 1 



CH 3 



CHaO/ 



Thebaine 



(C l6 H 12 0) : N . CH 3 

 HC1 



dilute 



-> Thebenine <- 



CH 3 0' 



0=. 



HC1 



(C, 6 H.,0) : N . CH 3 



dilute 



Codeinone 



Morphothebaine 



CH 3 G 



CH 3 



HO 



HO 



Thebaol 



