Ryan and Walsh — On Desoxy-Hydrocatechin- Tetramethy I- Ether. 117 



By condensing veratroyl chloride with ethylphloroglucinol-trimethylether 

 veratroyl-ethylphloroglucinol trimethylether was formed : — 



OCH 3 

 CH 3 0/\ CH 3 0/\OCH 3 



'\/ C0 -- I \/ I CH J .CH 3 



OCH3 



The compound obtained by reducing the latter substance with sodium and 

 alcohol should be identical with desoxy-hydrocatechin-pentamethylether if 

 the coumarane formula given to the catechin is correct. 



The reduction-compound, which we obtained by means of sodium and 

 alcohol, and also by the aid of amalgamated zinc and hydrochloric acid, was 

 an oil which resisted all attempts to crystallize it, even when its saturated 

 alcoholic solution was inoculated with one or two crystals of desoxy-hydro- 

 catechin-pentamethylether, which we prepared, for comparison, from catechin 

 by the method of von Kostanecki and Lampe. 



Owing to difficulty in obtaining a supply of phloroglucinol during the 

 past year, the amount of oily reduction compound in our hands was very 

 small, and from the failure to obtain the latter in a crystalline form it would 

 be somewhat premature to conclude that the formula attributed to desosy- 

 hydrocatechiii-pentamethylether is incorrect. 



Experimental Part. 

 1. Phloroglucinol- Trimethylether. 

 Phloroglucinol-trimethylether is obtained from Goto bark residue, but as 

 this source of the substance was not available during the past year, its 

 preparation was attempted by the direct methylation of phloroglucinol. 



Theamount of phloroglucinol at our disposal being small, preliminary experi- 

 ments were tried with a view to finding which of the various methods usually 

 employed for methylating phenols would in this case give the best results. 

 The yields of the trimethylether obtained by the action on phloroglucinol 



of: — 



(a) Potash and methyl iodide, 



(b) Silver oxide and methyl iodide, 



(c) Diazomethane, 



were poor, and it was finally found that the best yield (about 20 per cent, of 

 the theoretical) was got by the action of potash and dimethyl sulphate on the 

 compound. 



A solution of 15'7 grams of caustic potash and 15 grams of phloroglucinol 

 in 150 c.c. of water was placed in a large round flask, and heated on a water- 

 bath. Dimethyl sulphate (37'5 grams) was then gradually added to the 



