58 



THE ALUMNI JOURNAL, 



CHClo 



isomeric compound, iso-eugenol, which 

 results from heating eugenol in an alkali 

 solution, also yields vanillin under the 

 same circumstances. Usually derivatives 

 of, and not eugenol itself, are employed, 

 those compounds in which the free 

 hydroxyl group (of eugenol) contains 

 substituting groups which are readily re- 

 moved by oxidation, being preferred , for 

 example, acetyl eugenol 



/C3H, 

 C6H3— OCH3 



\0— CH3CO 



is readily oxidized by permanganate to 

 acetyl-vanillin, which on saponification 

 yields vanillin. 



In place of the acetyl derivatives a 

 a number of other eugenol derivatives 

 have answered the same purpose. Messrs. 

 Auger and Boissieu by the action of me- 

 thylene chloride on eugenol sodium, pre- 

 pared a methylene-bi-eugenol, this on 

 oxidation yielded methylene-bi-vanillin, 

 which when converted into a hexa- 

 chloride derivative and treated with 

 hydrobromic acid yielded vanillin. 



CH3O— yCeH, 



CH=< 



.0 



O 



/ 



'CfiH, 



CH3O- 

 CH^^CH— CH/ 



Methylene-bi-eugenol. 



COH. 

 CH3. O— ^CeH, 



O 



CHn/ 



CH3.O— >CeH3 



COH^ 



Methylene-bi-vanllliu, 



/ 



CH3 O— >CeH, 



X, 



o 



CO., 



\ 



/ 



CH3.0 — .C6H3 

 CH Cl/ 



Methylene-vanillin-hexa-chloride. 



COH 



CH3 O — ^CeHj 



OH 

 OH. 



CH3. O — .CeHs 



COH 



2 mol. Vanillin. 



Messrs. Boehringer & Co. introduce a 

 benzyl rest into the hydroxyl group of 

 eugenol, then by heating with potassium 

 hydrate, the iso-compound is produced, 

 this on oxidation yields benzyl- vanillin, 

 which on heating with hydrochloric acid 

 gives rise to vanillin, thus : 



/CH3— CH=CH2 

 CeH,— O.CH3 

 \O.CHAH5 



Benzyl Eugenol. 



/CH=CH— CH. 

 C6H3 — O.CH3 



XO.CHAHs 



Benzyl -iso-eugenol. 



/COH 

 CeH3-O.CH3 



XO.CHAHb 



Benzyl vanillin. 



/COH 

 C^Hs— O.CH3 

 \0H 



Vanillin. 



(To be continued.) 



Aromatic spirit of ammonia has had its 

 oil of allspice replaced by oil of nutmeg. 



