21 1-22.] 



METHYLPROPYL CARBINOL 



79 



can be converted into the n-amyl 

 chloride (i-chlorpentane), and the latter 

 on heating with acetic acid and potas- 

 sium acetate to 300 gives (with amyl 

 acetate) normal amylene (propylethy- 

 lene) (Schorlemmer, Ann. 161, 269), 

 which combines with hydrogen iodide 

 to form 2-iodopentane (Wurtz, Ann. 

 148, 131 : see also Wagner and Sayt- 

 zeff, Ann. 178, 313; Wischnegradsky, 

 Ann. 190, 347), from which the alcohol 

 can be obtained as under P. Normal 

 amylene is also among the amylenes 

 obtained from the amyl alcohols of 

 fusel oil by the action of zinc chloride 

 (Wischnegradsky, Journ. Russ. Soc. 9, 

 192). 



[J.] From normal propyl alcohol [15] 

 and acetic acid [Vol. II] by the action 

 of zinc propyl (Gladstone and Tribe, 

 Ber. 6, 1 136; Schtscherbakoff, Bull. Soc. 

 "2] 37, 345) on acetyl chloride (Mar- 

 ownikoff, Bull. Soc. [2] 41, 259 ; 

 Wagner, Journ. Russ. Soc. 16, 333). 

 Ethyl alcohol is formed at the same 

 time. 



[K.] From normal pentane (see under 

 n-amyl alcohol [20 ; B ; C ; D, &c.]) 

 by chlorination (Schorlemmer, Ann. 

 161, 268) and conversion into the al- 

 cohol by usual methods. The i-chlor- 

 pentane formed also during chlorination 

 can be converted into 2-pentanol through 

 propylethylene as under I. 



NOTE : All generators of n-hexane are gener- 

 ators of pentane (see under n-amyl alcohol [20 ; 

 G]) and therefore of 2-pentanol. The generators 

 of hexane (see under n-hexyl alcohol [23] 

 are : mannitol [51] ; glycerol [48] ; glutaric arid 

 [Vol. II] ; cetyl alcohol [33] ; myristic acid [Vol. 

 II] ; stearic acid [Vol. II] ; adipic acid [Vol. II] ; 

 n-butyric acid [Vol. II], and aromatic compounds 

 (see under n-hexyl alcohol [23 ; A]). 



[L.] From tartaric and butyric acids 

 [Vol. II] through pyroracemic acid (see 

 under benzyl alcohol [54; N]), the 

 potassium salt of which mixed with 

 potassium butyrate gives methylpropyl 

 ketone on electrolysis (Hofer and Uhl, 

 Ber. 33, 654). Subsequent steps as 

 above under A. 



NOTE : The generators of pyroracemic acid 

 referred to under benzyl alcohol [54] are thus, 

 with butyric acid, generators of this amyl 

 alcohol. These are : ethyl alcohol and hydrogen 

 cyanide [14 ; 172] ; acetic acid or acetoacetic acid 

 and hydrogen cyanide ; citric acid ; propionic acid ; 

 lactic acid ; n- or isopropyl alcohol [15 ; 16], 



[M.] From dextrose [154], lavulose 



E155] or mannose [156], and acetic acid 

 Vol. II] through laevulic acid (see 

 under erythritol [50; H; I]), the 

 potassium salt of which when electro- 

 lysed in solution with potassium acetate 

 gives methylpropyl ketone (Hofer and 

 Uhl, Ber. 33, 656). 



NOTE : The following generators of laevulic 

 acid referred to under erythritol [50] thus 

 become with acetic acid generators of this amyl 

 alcohol : isohexoic acid ; malonic acid and glycerol 

 [48] ; acetic aldehyde [92] ; methylheptenone [111] ; 

 dimelhylheptenol [35]. 



The synthetical methylpropyl carbinol is 

 inactive, but is resolved into the 1-modification 

 by Penicillium glaucum (LeBel, Comp. Rend. 89, 

 312 ; Ber. 12, 2163 ; Jahresber. 1879, 492). 



22. Isoamyl Alcohol ; Isobutyl Car- 

 binol; Inactive Amyl Alcohol 

 of Fermentation ; 2-Metliyl-4- 

 Butanol. 



CH 3 . CH(CH 3 ) . CH 2 . CH 2 . OH 



NATUEAL SOURCES. 



Occurs as ester of angelic and tiglic 

 acids in Roman oil of chamomile from 

 Anthemis nobilis (see under isobutyl 

 alcohol [18]) ; occurs also in oil of 

 Eucalyptus globulus (Bouchardat and 

 Oliviero, Bull. Soc. [3] 9, 429). An 

 amyl alcohol (? this one) has been found 

 in American oil of peppermint (Schim- 

 meFs Ber. April, 1894 ; Ch. Centr. 

 1896, 2, 977). 



Esters of amyl (probably isoamyl) 

 alcohol occur in the oils of Eucalyptus 

 macrorrkyncha, E. aggregata, E. patenti- 

 nervis, &c. (Smith and Baker, Proc. 

 Roy. Soc., N. S. Wales, July, 1898; 

 Smith, Ibid. June, 1900; 'Nature/ 62, 

 384 ; SchimmeFs Ber. April, 1901 ; Ch. 

 Centr. 1901, 1, 1007). 



A secondary product of alcoholic fer- 

 mentation, this alcohol being the chief 

 constituent of various fusel oils (Scheele, 

 CrelFs Ann. 1785, 1, 61 ; Pelletan, 

 Ann. Chim. 30, 22 1 ; Berz. Jahresber. 

 6, 264 ; Dumas, Ann. Chim. 56, 314 ; 

 Ann. 13, 80 ; Cahours, Ann. Chim. 7O, 

 8 1 ; 75, 193; Ann. 37, 164; Dumas 

 and Stas, Ann. Chim. 73, 128 ; Balard, 

 Ibid. [3] 12, 294 ; Ann. 52, 311; Pas- 

 teur, Comp. Rend. 41, 296 ; Ann. 96, 



