Suhstituted Aliphatic Alcohols. 373 



was also used in the preparation of the glycol diacetate. One 

 mole of ethylene dibromide and two moles of freshly fused 

 potassium acetate were refluxed in a solution of eighty-hve per 

 cent alcohol on a water bath for eighteen to twenty liours, and 

 filtered to remove the potassium bromide. The filtrate was 

 fractionated to remove the alcohol and the glycol diacetate 

 was collected at 185°-187°. 



The ethylene glycol was produced by the hydrolysis of ethy- 

 lene glycol diacetate according to the method of Haller,"^ the 

 process being carried out as described by Louis Henry,f and 

 the yields corresponded to those given by Gattermann.:^ 



/3-Hydroxy-etliyl acetate was first prepared by Atkinsong 

 by heating on a boiling water bath for two days equi molecular 

 quantities of ethylene dibromide and potassium acetate in a 

 solution of eighty -five per cent ethyl alcohol. De Mole|| 

 claimed a considerable yield of the monacetin of ethylene gly- 

 col by heating for eighteen hours at the boiling temperature 

 an equimolecular mixture of ethylene dibromide and freshly 

 fused potassium acetate in an eighty to eighty-five per cent 

 solution of ethyl alcohol. Lourengo^f obtained this ester by 

 heating equimolecular quantities of ethylene glycol and glacial 

 acetic acid for one day in a sealed tube at 200°. 



The above method of Atkinson and De Mole was employed 

 with the hope of obtaining the yS-hydroxy-ethyl acetate. Three 

 hundred grams of ethylene dibromide were treated with 155 

 grams of water-free potassium acetate in 300 grams of 85 per 

 cent ethyl alcohol. This mixture was digested for twenty 

 hours in a flask fitted with a reflux condenser on a boiling 

 water bath. The potassium bromide which precipitated was 

 filtered off, and the filtrate fractionated to remove the alcohol. 

 A yield of 83 grams of diacetate was obtained, but no monace- 

 tin was formed, as no reaction took place on treatment of a 

 portion with acetyl chloride. 



On treating 300 grams of ethylene dibromide w^ith 310 

 grams of anhydrous potassium acetate in 300 grams of 85 per 

 cent ethyl alcohol, digesting for twenty-four hours, filtering, 

 and fractionating the filtrate, a yield of 174: grams of glycol 

 diacetate was obtained. This result is in accordance with the 

 experience of Louis Henry. "^^ who states that the diacetate is 

 obtained by treating ethylene dibromide with fused potassium 

 acetate, as described above. This method was tried repeatedly, 



*Haller, Compt. rend., cxliii, 657, 1906. 



f Henry, Bnll. Acad. Eoy. Belg. cl. sci. (3), xxxii, 402-417, 1896. 



X Gattermann, Prac. Methods of Org. Chem. 3ded., pp. 197-198, 1915. 



§ Atkinson, Ann. d. Chem. u. Pharm., cix, 232, 1859. 



I De Mole, Ber. d. d. Chem. Gesell., vii, 641, 1874. Ami. d. Chem. u. 

 Pharm. clxxiii, 117, 1874; clxxvii, 147, 1875. 



^ Lonren§o, Compt. rend.. 1, 91, 1860 Ann. d. Chem. u. Pharm., cxiv, 

 122, 1860. 



** Henry, Ann. d. chim. et d. Phys. (4), xxvii, 250, 1872. Eec. d. trav. 

 chim. d. Pays-Bas, xx, 243-254, 1901. Bull. Acad. Eoy. Belg. cl. sci. (3), 

 XXX vni, 236-248, 1901. 



