60 



ALCOHOLS 



[15 E-L. 



acid through a-chlorlactic, glyceric, and 

 pyrotartaric acids as above under A. 



Or from glycerol and potassium cyanide 

 [172] through allyl chloride and pyro- 

 tartaric nitrile and acid (dipentene [9; 

 G]) and then as under A above. 



[F.] Erythritol [50] gives 2-iodo- 

 butane on heating with aqueous hydr- 

 iodic acid (De Luynes, Bull. Soc. [2] 

 2, 3; Ann. 125, 252). Subsequent 

 steps through propane as above under C. 



[G.] From mannitol [5l] through 

 secondary hexyl iodide = 2-iodohexane 

 by heating with aqueous hydriodic acid 

 (Wanklyn and Erlenmeyer, Jahresber. 



1861, 731 ; 1862, 480 ; Zeit. 1861, 606 ; 



1862, 641; Ann. 135, 130; Domac, 

 Monats. 2, 310 ; Hecht, Ann. 165, 146 ; 

 209, 311; Uppenkamp, Ber. 8, 55; 

 Schorlemmer, Ann. 199, 139 : accord- 

 ing to Combes and LeBel, Bull. Soc. 

 [3] 7, 551, the iodohexane thus formed 

 is 3-iodohexane). Propane is among 

 the products formed by heating 2-iodo- 

 hexane with aluminium chloride to 225 

 (Lothar Meyer, Ber. 27, 2766; Kluge, 

 Ann. 282, 227). 



Or from mannitol through acrolt'in 

 and acrylic acid (see under benzyl alcohol 

 [54; AA and E]). From the latter 

 through a-chlorlactic acid, glyceric acid, 

 and pyrotartaric acid as above under A. 



[H.] From formic aldehyde [9l] 

 through ' oxymethylene/ which results 

 from its polymerisation (see under 

 formic aldehyde). Oxymethylene gives 

 n-propyl alcohol by dissolving in strong 

 sulphuric acid and distilling the product 

 with water (Gustavson, Journ. pr. Ch. 

 [2] 36, 301). 



Or oxymethylene forms a compound 

 with zinc ethyl which is decomposed by 

 water with the formation of n-propyl 

 alcohol (Tischtschenko, Journ. Russ. 

 Soc. 19, 483). 



[I.] From crotonic aldehyde [102] 

 through crotonic acid (see under benzyl 

 alcohol [54; H]). The acid combines 

 with hydrogen bromide to form ct-brom- 

 butyric acid (Naumann, Ann. 119, 115; 

 Wislicenus and Urech, Ann. 165, 93 ; 

 Ley, Journ. Buss. Soc. 9, 129; Tupoleff, 

 Ann. 171, 249 ; Hemilian, Ann. 174, 

 325). The latter, on distillation of the 

 potassium salt with a solution of sodium 



nitrite, gives nitropropane (Auger, Bull. 

 Soc. [3] 23, 333), which can be reduced 

 to propylamine and treated as above 

 under A. 



Or from crotonic acid, the ester of 

 which condenses under the influence of 

 sodium ethoxide to form dicrotonic ester, 

 from which the acid can be obtained by 

 hydrolysis. Dicrotonic acid gives pyro- 

 tartaric acid on oxidation by alkaline 

 permanganate (v. Pechmann, Ber. 33, 

 3323). From pyrotartaric acid as above 

 under A. 



[ J.] From acetic aldehyde [92] through 

 butyrochloral and allylene dichloride 

 (see under benzyl alcohol [54; H]). 

 The dichloride on heating with water at 

 1 80 gives acrylic acid (Pinner, Ber. 7, 

 66). Subsequent steps through a-chlor- 

 lactic acid, glyceric, and pyrotartaric 

 acids as above under A. 



Or from acetic aldehyde through 

 crotonic aldehyde [102] and crotonic 

 acid and then as above under I. 



Aldehyde and hydrogen cyanide [172] 

 give a cyanhydrin which, by the ac- 

 tion of phosphorus pentachloride, gives 

 a-chlorpropionitrile, from which a-chlor- 

 propionic acid can be obtained by 

 hydrolysis. The acid on heating with 

 barium hydroxide solution gives acrylic 

 acid (Michael and Garner, Ber. 34, 

 4049). 



[K.] Acetone [106] gives propane on 

 heating in a sealed tube with strong 

 aqueous hydriodic acid (Berthelot, Bull. 

 Soc. [2] 7, 69). From propane as 

 above under A. Or acetone on chlorina- 

 tion gives I : I -dichloracetone (Fittig, 

 Ann. 110, 40; Borsche and Fittig, 

 Ann. 133, 112), which gives acrylic acid 

 on boiling with potassium carbonate 

 solution (Faworsky, Journ. pr. Ch. [2] 

 51, 555). From acrylic acid through 

 pyrotartaric acid as above under A. 



Or from acetone, acetic acid, and 

 ethyl alcohol through acetylacetone and 

 methylpropyl ketone (as under n-pri- 

 mary amyl alcohol [20 ; B ; C] and n- 

 secondary amyl alcohol [21 ; D]). From 

 the ketone through the oxime to propyl- 

 amine as below under AA. 



[L.] Pttlegone [128] gives pyrotar- 

 taric acid among the products of its oxi- 

 dation by potassium permanganate (Mar- 



