116 Scientific Proceedings, Royal Dublin Society. 



which is based on their formula for catechin, and on the analogy between their 



experiment and that by which Hans Alexander 1 converted coumarane into 



o. ethylphenol. 



By the action of sodium and alcohol on coumarone, Alexander obtained 



coumarane as primary product, and the phenol as secondary product. 







/\/\CH /\/\CBU /\OH 



\/ CH \/ CH 2 \/CH 2 . CH 3 



Coumarone. Coumurane. o - Ethyl-Phenol. 



Desoxy-hydrocaLechin-tetramethylether, which is soluble in alkali, was 

 further methylated by von Kostanecki and Lampe, forming a well-crystallized 

 pentainetbylether, which melted at 83°-84° C. 



If, however, the chromane formula be assumed correct, the desoxy-hydro- 

 catecbin-pentamethylether will be represented by 



och 3 

 CH3O /\ OCH 3 /\,OCH 3 



II CH 3 . CH 2 . CH 2 — I' 



OCH 3 



As the synthesis of dimethoxy-y-phenylpropyl-phloroglucinol-trimethyl- 

 ether seemed more difficult to realize than that of 3-ethyl-2.4.6.3'.4'-penta- 

 methoxy-diphenyl-methane, we attempted the synthesis of the latter in 

 preference to that of the former substance. 



Vanillin was converted by means of potash and dimethyl sulphate into 

 veratric aldehyde, and the latter was oxidised by potassium hypobromite to 

 veratric acid. Veratroyl chloride was prepared from the acid by means of 

 thionyl chloride. 



Since Coto bark residues were not available, we were obliged to prepare 

 phloroglucinol-trimethylether directly from phloroglucinol, and after several 

 experiments we found that the best method of effecting this operation was by 

 a slight modification of that described by J. Herzig and Br. Erthal. 2 



Following the procedure previously employed by von Kostanecki and 

 Tambor 3 for the preparation of phloracetophenone-trimethylether, the latter 

 substance was obtained, and this on reduction with amalgamated zinc and 

 hydrochloric acid was converted into the ethyl homologue of phloroglucinol- 

 trimethylether : — 



CH 3 0/\()CH 3 CH 3 0/\OCH 3 



I I -> I I 



\/CO . CH 3 \/CH 2 . CH 3 



OCH3 OCH 3 



1 Ber. d. Deutsch. Chem. Ges., 1892, xxv., p. 2409. 



3 Monatsh. f. Cheraie, 1911, xxxii., p. 481. 



3 Ber. d. Deutsch. Chem. Ges., 1899, xxxii., p. 2262. 



