46 Proceedings of the Royal Irish Academy. 



Experimental Part. 

 Prefaration of chloride of cniechin tetramethyl ether. 

 Seven grams of pure cafcechia tetramethyl ether were dissolved in 50-60 c.c. 

 of carbon disulphide in a 200 c.c. round flask fitted with a reflux condenser 

 and calcium chloride tube; 5 grams of phosphorus pentachloride were added 

 to the contents of the flask (by disconnecting the condenser for a few 

 moments). 



An evolution of hydrogen chloride was immediately observed. The flask 

 was shakenintermittently until all the phosphorus pentachloride had dissolved 

 and the evolution of hydrogen chloride ceased (about ten minutes in all). 



The contents of the flask were then thrown into a litre beaker containing 

 200 c.c. of 10 per cent, sodium carbonate solution with some ice. The contents 

 of the beaker were stirred vigorously until effervescence ceased. The layer of 

 carbon disulphide was separated in a large separation funnel, and was washed 

 again by shaking up with 100 c.c. 10 per cent, carbonate solution. Finally, 

 the carbon disulphide layer was allowed to stand for half an hour in a conical 

 flask over 10 grams of anhydrous potassium carbonate. The carbon disulphide 

 was then decanted off and allowed to evaporate in a dish. When most of the 

 solvent had gone, colourless rhombohedral crystals separated. These were 

 pressed on the filter pump and allowed to stand on a porous plate for half an 

 hour until all the solvent had gone. The compound was recrystallized from 

 ligroin. 



The pure compound melted at 112" C. with evolution of hydrogen chloride. 

 The yield of the pure product was 6 grams. 



In air estimation of chlorine by Stepanow's method : — 



0"4640 grams of chloro-catechin tetramethyl ether required 12-9 c.c. 

 of N/10 AgNOj for titration, corresponding to 0'0457 grams of 

 chlorine. Therefore CI for compound is 9'85. 

 CigH^iOjCl requires CI 9-724. 



Freparution of ethyl catechin tetra'tnethyl ether. 



A solution of 5 grams of chlorocatechin tetramethyl ether in 40-50 c.c. of 

 absolute alcohol was boiled for half an hour in a (100 c.c.) round flask fitted 

 with a reflux condenser. The contents of the flask were then poured into a 

 dish and left aside for a few hours until the separation of felted crystals was 

 complete. The crystals were separated from the mother liquor on a Buchner 

 filter in the usual way. After recrystallizing twice Jrom absolute alcohol and 

 once from ligroin, the melting point of the compound was 123° C. The yield 

 of the pure compound was 2-5 grams. 



