400 On Coniferine and its Conversion. [June 18, 



Indeed, submitted under pressure to the action of hydrochloric acid, 

 vanilline splits into chloride of methyl and protocatechuic aldehyde, 



/OCH 3 /OH 



C 6 H 3 <-OH + HC1 = CH 3 C1 e3 



H \o H. 



A corresponding action takes place with hydriodic acid ; but in this 

 case the aldehyde is destroyed. 



An additional proof of the correctness of our view regarding the con- 

 stitution of vanilline is obtained by treating this substance with acetic 

 anhydride and benzoyl chloride. 



The action does not go beyond the formation of the compounds 



/OCH 3 



NO OH, 



and 



,/OCH 3 



\COH, 



showing that vanilline does not contain more than one hydroxylic 

 group. 



The constitution of vanilline being thus made out, there could be no 

 doubt regarding the structure of the product of fermentation from which 

 vanilline arises. This compound is the ethylic ether of vanilline, 



/OCH 3 



C a H 3 f-OC 2 H 5 



\COH. 



That such is the constitution of the body is proved by the simultaneous 

 formation of ethylic aldehyde when vanilline is formed.' We obtained, 

 however, an additional confirmation of this conception by submitting the 

 product of fermentation to the action of hydriodic acid under pressure, 

 when an alcohol iodide was formed, which we succeeded in separating 

 into the iodides of methyl and ethyl, 



/OCH 3 /OH 



C 6 H 3 ^-OC 2 H 5 + 2HI = CH 3 I + C 2 H 5 I + C 6 H 3 ^OH 

 \COH \COH. 



The experiments we have described in this note were performed in the 

 laboratory of Professor A. W. Hof maim, to whom we are deeply indebted 

 for the advice and assistance he has given us in the course of these 

 researches. 



