76 



ALCOHOLS 



[19 H-20 H. 



120, 286 ; Zelinsky, Ber. 20, 2026 ; 

 Michael and Graves, Ber. 34, 4044) 

 gives brompropionyl bromide (Kaschir- 

 sky, Journ. Russ. Soc. 13, 81), which 

 by interaction with zinc methyl yields 

 dimethylisopropyl carbinol (Ibid. 82). 



[I.] From lactic acid [Vol. II] and 

 methyl alcohol [13]. Lactic acid re- 

 acts with hydrogen bromide to form 

 a-brompropionic acid (Kekule', Ann. 

 130, 16). Subsequent steps as above 

 under H, &c. 



[J.] From diacetyl [113] and methyl 

 alcohol [13] through pinacone by the 

 interaction of magnesium methiodide 

 and the former (Zelinsky, Ber. 35, 2138). 

 From pinacone through pivalic acid as 

 above under D. 



20. Normal Primary Amyl Alcohol ; 



Normal Butyl Carbinol ; 



1-Feutanol. 



CH, . CH . CH 9 . CH, . CH . OH 



NATURAL SOURCES. 



Said to occur in certain fusel oils 

 (Wischnegradsky, Ann. 190, 350) and 

 among the products of fermentation of 

 glycerol by Bacillus butylicus (Morin, 

 Bull. Soc. [2] 48, 803). 



SYNTHETICAL PROCESSES. 



[A.] From normal valeric (pentanoic) 

 acid [Vol. II] through the aldehyde 

 [95] by distillation with a formate 

 (Lieben and Rossi, Ann. 159, 70) and 

 reduction with- sodium amalgam (Ibid.). 



NOTE : The generators of valeric aldehyde 

 given under this compound are : succinic acid ; 

 fumaric acid ; adipic acid ; stearic acid (all 

 through sebacic acid) ; and n-hexoic acid. 



[B.] From acetic acid [Vol. II] by 

 combining acetyl chloride with alu- 

 minium chloride, decomposing the pro- 

 duct with water (Combes, Ann. Chim. 

 [6], 12, 207), and reducing the acetyl- 

 acetone (2 : 4-pentanedione) thus formed 

 to n-pentane by heating with hydriodic 

 acid (Combes, loc. cit. 233). Normal 

 pentane gives i-chlorpentane (together 

 with 2-chlorpentane) on chlorination 



(Schorlemmer, Ann. 161, 268 ; Lacho- 

 wicz, Ann. 220, 191), and the corre- 

 sponding alcohol is obtained by con- 

 version into amyl acetate and hydrolysis 

 (ffid.). 



NOTE : Normal pentane might also be syn- 

 thesised from methyl [13] and n-butyl [17] 

 alcohols or from ethyl [14] and n-prc-pyl [15] 

 alcohols by acting upon mixtures of the alkyl 

 iodides with sodium (Wurtz, Ann. Chim. [3] 

 44, 275 : see also under heptane [2 ; A]). 



[C.} From acetone [106], acetic acid 

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

 acetylacetone by the action of sodium 

 on a mixture of acetone and ethyl 

 acetate (Claisen and Ehrhardt, Ber. 22, 

 ion ; Claisen, Ann. 277, 168), reduc- 

 tion to pentane, &c., as under B. 



[D.] From pyridine or piperidine 

 [Vol. II] through n-pentane by heat- 

 ing with hydriodic acid to over 300 

 (Hofmann, Ber. 16, 590 ; Spindler, 

 Journ. Russ. Soc. 23, 39) and then as 

 under B. 



[E.] From normal hexoic acid [Vol. II] 

 by the action of iodine on the silver 

 salt (Simonini, Monats. 13, 316) and 

 hydrolysis of the amyl hexoate formed. 



Or from n-hexoic acid through n- 

 amylamine (i-aminopentane) by the 

 action of bromine in presence of potash 

 on the amide of the acid (Hofmann, 

 Ber. 15, 770), followed by the action of 

 nitrous acid on the amine (Gartenmeister, 

 Ann. 233, 253). 



[F.] From adipic acid [Vol. II] 

 through sebacic acid by electrolysis of 

 potassium ethyl adipate and hydrolysis 

 of the ester (Crum Brown and Walker, 

 Ann. 261, 120). Sebacic acid when 

 distilled with lime is said to give 

 among other products valeric aldehyde 

 (Calvi, Ann. 91, no; Petersen, Ann. 

 103,184; Dale and Schorlemmer, Ann. 

 199, 149), which can be treated as 

 under A. 



[G.] From mannitol [5l] through 

 n-hexane (see under n-hexyl alcohol 

 [23 ; B]). The latter gives pentane 

 on heating with aluminium chloride 

 (Friedel and Gorgeu, Comp. Rend. 127, 

 590). Subsequent steps as under B 

 above. 



[H.] From glycerol [48] through 

 diallyl and hexane (see under n-hexyl 



