120 Scientific Proceedings, Royal Dublin Society. 



heated on the water-bath, under a reflux condenser, until the evolution of 

 hydrochloric acid had ceased. The flask was allowed to stand over-night, and 

 its contents were then added to ice-cold, acidulated water. The unchanged 

 phloroglucinol-trimethylether was distilled in a current of steam ; the 

 residue left in the distillation flask was filtered, washed with a little warm 

 aqueous alkali, and recrystallized a few times from alcohol. It melted at 

 123°-124° C, and gave on analysis the following results : — 



01097 substance gave 0-2680 CO2 and 0-0660 H 2 0, 



corresponding to C 66'63, H 6-68, 



C ao H 24 G requires 66'66, H 6-66. 

 Veratroyl-ethylphloroglucinol-trimethylether crystallizes from alcohol in 

 colourless plates, which are insoluble in water or dilute alkali, and soluble in 

 chloroform, alcohol, ether, or benzene. 



6. Reduction of Veratroyl-Ethylphloroglucinol-Trimethylether. 



(a) Sodium and Alcohol. — A solution of - 55 grams of veratroyl-ethyl- 

 phloroglucinol-trimethylether in 50 c.c. of absolute alcohol was heated to 

 boiling under a reflux condenser, and 2 grams of sodium were added rapidly 

 in small portions, through the tube of the condenser. When all the sodium 

 had dissolved the excess of alcohol was removed by distillation in a current 

 of steam. The oily residue in the distillation flask was extracted with ether, 

 the ethereal layer was washed with dilute alkali, dried, and allowed to 

 evaporate. The oil, which remained, was very soluble in the usual organic 

 solvents, such as ether and alcohol. On prolonged standing in the air or in a 

 vacuum desiccator, with or without addition of solvents, it did not crystallize. 



(b) Amalgamated Zinc and Hydrochloric Acid. — Veratroyl-ethylphloro- 

 glucinol-trimethylether (0 - 85 gram) was reduced by means of amalgamated 

 zinc and hydrochloric acid by a method similar to that by which phloraceto- 

 phenone-trimethylether was converted into ethylphloroglucinol-trimethyl- 

 ether. The oily reaction-product was extracted with ether, the ethereal 

 solution was washed with dilute aqueous potash, dried, and allowed to 

 evaporate. As in the case of the reduction with sodium and alcohol the 

 small quantity of oil which was obtained was readily soluble in the ordinary 

 organic solvents, and could not be converted into a crystalline form. 



When a solution of the oil in the least possible quantity of absolute 

 alcohol was inoculated with one or two crystals of desoxy-hydrocatechin- 

 pentamethylether, which was prepared from catechin by the method 

 described by Von Kostanecki and Lampe, 1 and allowed to stand in a vacuum 

 desiccator, the substance did not crystallize. 



1 Ber. 4. Deutsch. Chem. Gee., 1907, xl., p. 720. 



