Substituted Aliphatic Alcohols. 375 



respective products. Glycol diacetate boils at 186°-187° and 

 ethylene glycol at 197°. From the molecular constitution of 

 the monacetin of ethylene glycol we wonld naturally expect 

 its boiling point to lie between those of ethylene glycol and 

 glycol diacetate. The boiling point of the main portion of the 

 product obtained by direct esterification was distinctly higher 

 than that given in the literature, and lies between that of the 

 glycol and of the diacetate. 



The /8-methoxy-ethyl acetate was prepared by treating the 

 y8-methoxy-ethyl alcohol with the theoretical quantity of acetyl 

 chloride. The ester, boiling at 14:4°-145°, was purified by 

 fractional distillation. This ester has been previously pre- 

 pared"^ by treating the corresponding alcohol with acetic anhy- 

 dride. 



The /3-methoxy-ethyl alcohol was obtained for the prepara- 

 tion of the yS-methoxy-ethyl acetate by preparing monosodium 

 glycollate, and treating it with the theoretical quantity of 

 methyl iodide under suitable conditions according to the method 

 of Palomaa.f A separation of the glycol-ether, boiling at 

 124°-126°, was effected by fractionation. 



The /3-ethoxy-ethyl acetate was prepared by treating /3-ethoxy- 

 ethyl alcohol with acetyl chloride. The excess of acetyl chlo- 

 ride was removed by fractional distillation, and the ester was 

 found to boil at 157°-158°. The alcohol used in this prepara- 

 tion was obtained by the method of Palomaa. The mono- 

 sodium glycollate was treated with ethyl iodide as described in 

 this method. Upon fractionation the alcohol distilled over at 

 134:°-135°, and possessed the properties given by PalomaaJ and 

 De Mole.§ 



The /S-ethoxy-ethyl alcohol was also obtained by a second 

 method which is not recorded in the literature, and appears here 

 for the first time. In attempting to prepare /S-ethoxy-ethyl 

 acetate by refiuxing equimolecular quantities of /8-brom-ethyl 

 acetate and sodium ethylate, it was found that y8-etlioxy- 

 ethyl alcohol was obtained. The materials were refluxed in a 

 water-free alcoholic solution for half an hour on a water bath. 

 On filtering from sodium bromide and fractionating the reac- 

 tion mixture, a product was obtained which had all the physi- 

 cal characters of the /3-ethoxy-ethyl alcohol. It also reacted 

 with acetyl chloride giving the /3-ethoxy-ethyl acetate. 



The yS-chlor-etliyl acetate was prepared by treating ethylene 

 chlorhydrin with acetyl chloride|| in slight excess of the theo- 

 retical amount. The pure ester, boiling at 143°-145°, was 

 obtained by fractionation. The y8-ethylene chlorhydrin for the 

 preparation of this ester was obtained according to the method 



* Palomaa, Ber. d. d. Chem.Gesell., xxxv, 3300, 1902. 



t Palomaa, ibid., xlii, 3873, 1909. 



i Palomaa, ibid., xlii, 3876, 1909. §De Mole, ibid., ix, 745, 1876. 



IIHenrv, Ber. d. d Chem. Gesell., vii, 70, 1874. 



