20H-21D.] NORMAL PRIMARY AMYL ALCOHOL 



77 



alcohol [23 ; C]) and pentane, &c., as 

 above. 



[I.] From glutaric acid [Vol. II] 

 through suberic acid and hexane (see 

 under n-hexyl alcohol [23; D]) and 

 then as above. 



NOTE : The following generators of suberic 

 acid referred to under n-hexyl alcohol [23] thus 

 become generators of hexane and therefore of 

 pentane and n-amyl alcohol : cetyl alcohol [33] ; 

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

 adipic acid [Vol. II) through sebacic acid; 

 azela'ic acid [Vol. II] through ketocyclo-octane. 



For aromatic generators of hexane see under 

 n-he"xyl alcohol [23 ; A]. 



[J.] From n-butyric acid [Vol. II] 

 through hexane (see under n-hexyl 

 alcohol [23 ; K]), pentane, &c., as above 

 under G. 



21. Metliylpropyl Carbinol ; 

 Normal Secondary Amyl Alcohol ; 



2-Peiitaiiol. 



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



NATURAL SOURCE. 



Said to occur in fusel oil (especially 

 Swedish) from potato starch spirit (Ra- 

 buteau, Comp. Rend. 87, 501). 



SYNTHETICAL PROCESSES. 



[A.] From acetic and butyric acids 

 [Vol. II] through methylpropyl ketone 

 (2-pentanone) by distillation of the 

 mixed calcium salts (Semljanitzin, 

 Journ. pr. Ck [2] 23, 263; Friedel, 

 Ann. 108, 124 ; Grimm, Ann. 157, 251) 

 and reduction with sodium amalgam 

 (Friedel, Jahresber. 1869, 513; Belo- 

 houbek, Ber. 9, 924). 



[B.] From methyl alcohol [13] and 

 butyric acid [Vol. II] by the action 

 of zinc methyl on butyryl chloride and 

 decomposition of the product with water 

 (Butleroff, Zeit. [2] 1, 614; Bull. Soc. 

 [2] 5, 17) and reduction of the methyl- 

 propyl ketone thus obtained as under A. 



[C.] From ethyl alcohol [14] by the 

 action of zinc ethyl on chloroform 

 (Beilstein and Rieth, Ann. 124, 245). 

 The amylene thus formed is probably 

 the symmetrical methylethylethylene 



(3-pentene), which can be converted 

 into 2-chlor- or 2-iodopentane, &c., as 

 under P. 



Or from ethyl alcohol and acetic acid 

 [Vol. II] through ethylacetoacetic ester 

 by the action of sodium and ethyl 

 iodide on acetoacetic ester (Geuther, 

 Jahresber. 1863, 324; Frankland and 

 Duppa, Journ. Ch. Soc. 4, 396 ; Wis- 

 licenus, Ann. 186, 187; Miller, Ann. 

 200, 281; Wedel, Ann. 219, 100), 

 methylpropyl ketone by heating with 

 potash or baryta (Frankland and Duppa, 

 Ann. 138, 2 1 6), and reduction as under 

 A. Or the ethylacetoacetic ester can 

 be reduced by sodium amalgam to 

 a-ethyl-/3-hydroxybutyric (2-pentanol- 

 3-methylic) acid (Waldschmidt, Ann. 

 188, 240), the latter decomposed by dry 

 distillation into a-ethylcrotonic acid 

 (Ibid. 245) ; then through the hydro- 

 bromide, 3-pentene, 2-chlorpentane, &c., 

 as under G. 



Also from acetic acid and ethyl alco- 

 hol through acetoacetic ester [Vol. II], 

 the y-chloro-derivative which is formed 

 (with the a-derivative) on chlorination 

 (Haller and Held, Comp. Rend. 108, 

 516), the y-cyano-derivative by the 

 action of potassium cyanide (I /.id.}, ace- 

 tonedicarboxylic ester, by the action of 

 hydrogen chloride on the y-cyano-deri- 

 vative dissolved in alcohol (Haller and 

 Held, Comp. Rend. Ill, 682), dimethyl- 

 acetonedicarboxylic ester, and subse- 

 quent steps as under H. Also from 

 ethyleneacetoacetic ester ("W. H. Per- 

 kin, junr., Ber. 16, 2136 ; 17, 1440) 

 through acetyltrimethylenecarboxylic 

 acid, acety Itrimethylene (ethanoyl-cy clo- 

 propane), and reduction of latter with 

 sodium amalgam (Marshall and W. H. 

 Perkin, junr., Trans. Ch. Soc. 59, 874). 



[D.] From acetone [106], acetic acid 

 [Vol. II], and ethyl alcohol [14] through 

 acetylacetone (see under n-primary 

 amyl alcohol [20; B and C]), ethyl- 

 acetylacetone by the action of ethyl 

 iodide on the sodium salt (Combes, 

 Ann. Chim. [6] 12, 247), methylpro- 

 pyl ketone by the action of potash 

 (Ibid. 248), and reduction as under A. 



Or the acetylacetone can be converted 

 directly into 2-iodopentane by heating 

 with hydriodic acid (Combes, Ann. 



