Ryan and Dillon- — On Higher Tertiary Alcohols. 243 



Action of Methyl Steauate on Magnesium and Naphthyl Bkomide. 



2"7 grammes of magnesium, 34-5 grammes of bromnaphthalene, and 50 c.c. 

 dry ether were taken in a conical flask fitted with a reflux condenser. Three 

 or four drops of methyl iodide and a trace of iodine were added, and the 

 mistiu'e was warmed. After about two hours a reaction set in, and when the 

 magnesium had all dissolved, 15 grammes of methyl-stearate were added. The 

 ester began to react with the Grignard compound after about five minutes ; and 

 the change was soon completed, leaving a green gelatinous mass in the flask. 

 This was left standing over-night, and in the morning was warmed on the water- 

 bath. Water was added with cooling, though the evolution of heat was less 

 than in the reactions previously described. The mixture was made acid with 

 liydrochloric acid, the ether was evaporated off, and the oily organic layer, 

 which did not solidify on cooling, was separated from the water and distilled 

 with steam. The distillate consisted of naphthalene and unchanged brom- 

 naphthalene. The residue in the flask was treated in the usual manner for 

 the removal of unchanged ester and extracted with benzene. The benzene 

 extract was then dissolved in alcohol, the solution was decolorized ^vith 

 animal charcoal, and the product was recrystallized from alcohol. 



The compound was a yellowish-white solid melting at 55° C. 



0'1831 gramme gave on analysis 0'572 gramme of CO2 and 0-1757 

 gramme of HoO, corresponding to carbon, 85'6 per cent. ; hydrogen, 

 10-73 per cent. 

 C10H7 . CO . C1-H35 rec[uu:es : carbon, 85-2 per cent.; hydrogen, 10-73 per 

 cent. 



Peepaeation of Diethyl-Heptadecyl-Caebinyl Acetate. 



1*01 gramme of alcohol was dissolved by gently warming with 4 c.c. of 

 acetyl chloride, hydrochloric acid being evolved during the process. The 

 solution was left standing in a closed flask for two days, and was then poured 

 into water. The oil which separated was extracted with ether ; the ether 

 solution was washed with diluted sodium carbonate, dried over sodium sulphate 

 and evaporated. The residue was dissolved in benzene and filtered. On 

 evaporation of the benzene, 0-8682 gramme of an oily liquid was obtained 

 which solidified on cooling in iced water. 



The ester number was determined by boiling with excess of potash. 



iST 

 0-8682 gramme required for hydrolysis 4-73 c.c. of - alcoholic potash, 



corresponding to ester number, 152*5. 

 The ester number of CH,, . CO . OC..H„ is 152-17. 



B.I.A. l-EOC, VOr. XXIX., SECT. 1'.. [2 M] 



