64 



ALCOHOLS 



[15 AA-16. 



iodide tli rough ethylaeetoacetic ester 

 and methyl-n-propyl ketone (see under 

 n-secondary amyl alcohol [21 ; C]). The 

 oxime of the ketone on heating- to 1 00 

 with a solution of hydrogen chloride in 

 acetic acid (with a little acetic anhydride) 

 gives propylamine. Other acids, acetyl 

 chloride, or phosphorus pentachloride 

 bring about a similar decomposition 

 (Beckmann, Ber. 20, 2580; Hantzsch, 

 Ber. 24, 4018). From propylamine as 

 above under A. 



Or from acetoacetic ester through 

 crotonic acid (54 ; I). From the latter 

 through a-brombutyric acid and nitro- 

 propane, or through pyrotartaric acid as 

 above under I. 



Or acetoacetic ester on bromination 

 under appropriate conditions gives y- 

 bromacetoacetic ester (Duisberg, Ber. 

 15, 1379; Ann. 213, 138; Conrad and 

 Schmidt, Ber. 29, 1045 : see a ^ so Haller 

 and Held, Comp. Rend. 114, 452), and 

 this by the action of sodium ethoxide, 

 of alcoholic ammonia, or of sodium in 

 ethereal solution gives succinylsuccinic 

 ester (Wedel, Ann. 219, 94 ; Duisberg, 

 Ann. 213, 149 ; Conrad and Schmidt, 

 loc. cit. ; Mewes, Ann. 245, 74). From 

 succinylsuccinic ester through ethyl- 

 malonic acid as above under Y and O. 



Or dibromacetoacetic ester (see under 

 quinol [71; O]) gives dihydroxytere- 

 phthalic diethyl ester (Ibid.}. The latter 

 on reduction with zinc and hydrochloric 

 acid or with sodium amalgam gives 

 succinylsuccinic ester (Baeyer, Ber. 19, 

 432 ; Baeyer and Noyes, Ber. 22, 2168). 



Ethylaeetoacetic ester on treatment 

 with nitric acid gives I : i -dinitropropane 

 (Chancel, Jahresber. 1883, 1079), and 

 this when reduced in ethereal solution 

 with aluminium amalgam gives propyl- 

 amine and propionic aldehyde (Ponzio, 

 Journ. pr. Ch. [2] 65, 197)- 



[BB.] From thymol [67] through 

 thymoquinone, thymoquinol [82], and 

 dihydroxyterephthalic acid (see under 

 quinol [71 ; P]), and then through suc- 

 (tinylsuccinic acid, &c., as above. 



[CO.] From carvacrol [66] through 

 thymoquinone, &c. (quinol [71 ; Q]). 



[DD.] From malic acid [Vol. II] 

 through oxalacetic acid by oxidising 

 with hydrogen peroxide and a ferrous 



salt at a low temperature (Fenton and 

 Jones, Trans. Ch. Soc. 77, 77). From 

 oxalacetic acid through pyrotartaric or 

 through ethyl malonic acid as above 

 under Z. 



[EE.] From fumaric or male'ic acid 

 [Vol. II] through dibromsuccinic acid 

 (methane [l ; U]) and then through 

 oxalacetic acid, &c., via ethoxyfumaric 

 ester as above under Y. From oxal- 

 acetic acid through pyrotartaric or 

 ethylmalonic acid as under Z. 



[PP.] From allyl isothiocyanate [166] 

 through allyl cyanide and crotonic acid 

 (benzyl alcohol [54 ; J]). From crotonic 

 acid as above under I. 



[GG.] From glycocoll [Vol. II] and 

 ethyl alcohol [14] through n-propyl- 

 amine by distilling the hydrochloride of 

 the ethyl ester with sodium carbonate 

 (Schilling, Ann. 127, 97 ; Kraut, Ann. 

 177, 267 ; Hantzsch and Silberrad, Ber. 

 33, 70 ; Auger, Bull. Soc. [3] 21, 5 ; 

 see also Curtius and Jay, Ber. 27, 60 ; 

 Hantzsch and Metcalf, Ber. 29, 1684 ; 

 for production of propylamine see Curtius 

 and Goebel, Journ. pr. Ch. [2] 37, 163). 

 From propylamine as above under A. 



[HH.] From alanine [Vol. II] and 

 methyl alcohol [13] through acrylic acid 

 (benzyl alcohol [54; BB]). From 

 acrylic acid through a-chlorlactic acid, 

 glyceric acid, and pyrotartaric acid as 

 above under A (see also under benzyl 

 alcohol [54 ; I and P]). 



[II.] From lysine [Vol. II], pyro- 

 tartaric acid being a product of the 

 oxidation of the base by barium per- 

 manganate (Zickgraf, Ber. 35, 3401). 



16. Isopropyl Alcohol ; 



Dimethyl Carbinol ; 



2-Propanol. 



CH 3 .CH(OH).CH 3 



NATURAL SOURCE. 



Said to have been found as a secon- 

 dary product of fermentation in potato 

 fusel oil (Rabuteau, Comp. Rend. 87, 

 501). According to Victor Meyer and 

 Jacobson (Lehrb. d. org. Ch. I, 161 ; 

 see also Bouchardat, Ber. 7, Ref. 657) 

 this statement is erroneous. 



