118 Scientific Proceedings, Royal Dublin Society. 



solution, which was kept constantly stirred during the operation. When all 

 the dimethyl sulphate had been run in, potash and dimethyl sulphate were 

 again added in the same manner as before. The mixture was cooled, made 

 slightly alkaline, and distilled in a current of steam. The oily distillate was 

 reserved, and the residue in the distillation flask was acidified and extracted 

 with ether. On evaporating the ether an oily residue was obtained, which 

 was again methylated, and distilled with steam as before. The phloroglu- 

 cinol-trimethylether, which distilled with the steam as a colourless oil 

 crystallizing on standing, was filtered and dried in a vacuum desiccator. It 

 melted at 52°-53° C. The yield was 3 grams. 



2 . PMoracetophenone- Trimsthylether. 

 Phloraeetophenone-trimethylether was obtained from phloroglucinol- 



trimethylether by the method described by von Kostanecki and Tambor. 1 



Phloroglucinol-trimethylether (4 grams) was added to a solution of 



5 grams of acetyl chloride in 20 c.e. of dry carbon disulphide contained in 



a round flask of 200 c.c. capacity. Anhydrous ferric chloride (6'5 grams) 



was then added, and the mixture was heated on the water-bath under a 



reflux condenser, protected from atmospheric moisture by a calcium chloride 



tube until the evolution of hydrochloric acid ceased. The carbon disulphide 



was distilled, and the residue was washed with ice-cold, acidulated water. 



Hot water was added to a solution of the substance in boiling alcohol until 



the mixture became turbid. The solid, which was deposited on cooling, after 



recrystallization from dilute alcohol, melted at 99-100° C. The yield of the 



ketone was nearly quantitative. 



CH 3 0/\OCH 3 



I I 



3. EthylpMoToghicinol-Trimcthyldher. \/CH 2 . CH 3 



In a round flask of about 300 c.c. capacity, 15 grams of ordinary 

 granulated zinc were covered with a cold 5-per cent, solution of mercuric 

 chloride, and the mixture was allowed to stand for a few hours at the 

 temperature of the laboratory. The solution was poured off from the 

 amalgamated zinc, and the latter was used for the reduction without 

 further washing or drying. Phloracetophenone-trimethylether (3 grams), 

 water (30 c.c), and concentrated hydrochloric acid (15 c.c), were added to 

 the flask, and the contents were heated to gentle boiling under a reflux 

 condenser for six hours. At intervals during the process a mixture of eqiial 

 parts of concentrated hydrochloric acid and water was added to the contents 

 of the flask. The oily product of the reaction was extracted with ether, the 

 solvent was evaporated, and the residual oil was distilled in a current of 



1 Ber. d. Deutsoh. Ohem. Ges., 1899, xxxii., p. 2262. 



