Ryan and Walsh — On Desoxy-Hydrocatechin- Tetramethyl- Ether. 119 



steam. The oil contained in the distillate was converted, on standing, into a 

 colourless, crystalline solid, which, when dried in a vacuum desiccator, melted 

 at 29°-30° C, and gave on analysis the following results : — 



0-1771 substance gave 0-4353 C0 2 and 0-1404 H 2 0, 

 corresponding to C 67"02, H 7'92, 

 C„H 1G 3 requires C 67-35, H 8-16. 



Ethylphloroglucinol-trirnethylether in appearance resembles ( phloroglu- 

 cinol-trimethylether. It dissolves readily in the ordinary organic solvents, 

 such as alcohol and ether. It is insoluble in water or dilute aqueous potash. 



4. Veratroj/l-Chloride. 



Vanillin (25 grams) was converted into veratric aldehyde by dissolving it 

 in -32 c.c. of 25 per cent, aqueous potash, heating to boiling on a sand-bath, 

 and adding 45 grams of dimethyl sulphate in two instalments. The product 

 of the reaction was cooled, diluted with water, and extracted with ether. On 

 evaporation of the ether the aldehyde was deposited in the form of colourless 

 crystals. 



The aldehyde was oxidized to veratric acid by means of bromine and 

 potash. Veratric aldehyde (10 grams) was added to a solution of bromine 

 (10 grams) and potash (14 grams) in 200 c.c. of water. The mixture was 

 heated to boiling on a sand-bath, and kept constantly agitated by a current of 

 air which was aspirated through it. The heating was continued until the oil 

 had all dissolved. The solution was cooled, and after addition of 1 gram of 

 sodium bisulphite the veratric acid was precipitated by acidifying the solution 

 with hydrochloric acid. When recrystallized from boiling alcohol it melted at 

 17S°-180°C. 



The veratric acid (5 grams) was converted into veratroyl chloride by 

 heating with thionyl chloride (7 grams) until the reaction was finished. On 

 fractional distillation of the product the veratroyl chloride came over in the 

 neighbourhood of 290° C. as an oil, which quickly changed to a colourless 

 crystalline solid, melting at 68°-69 c C. 



5. Veratroyl-Etlvylphloroglucvtiol-Trimethylether. 



OCH 3 

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



\/ — C0 — \/CH 2 . CH 3 

 OCH3 



An intimate mixture of 2 - 5 grams of ethyl-phloroglucinol-trimethylether 



and 4 grams of veratroyl chloride was placed in a dry round flask, and 



covered with a layer of dry carbon disulphide. About 4 grams of powdered, 



anhydrous, resublimed aluminium chloride were added, and the mixture 'was 



