APPENDIX 



281 



135-160 gives isobutyl alcohol by 

 catalytic reduction (Sabatier and Sen- 

 derens, Comp. Eend. 137, 301). 



19. Tertiary Butyl Alcohol (p. 73). 



[B, p. 74.] Isobutyl alcohol gives 

 isobutylene as the only olefine by pyro- 

 genic ' contact * decomposition of its 

 vapour by heated alumina (Ipatieff, 

 Ber. 36, 2003). Isobutylene is absorbed 

 at o by aqueous hydrobromic acid with 

 the formation of tertiary butyl bromide, 

 which can be converted into the alcohol 

 by the usual processes (Ipatieff and 

 Ogonowsky, Ibid. 1988; Journ. Russ. 

 Soc. 35, 452). 



[K, p. 76.] From methyl alcohol [13] 

 and phosgene, formed by the combina- 

 tion of carbon monoxide and chlorine, 

 Magnesium methiodide and phosgene 

 interact with the formation of trimethyl 

 carbinol (Grignard, Comp. Rend. 136, 



21. Methylpropyl Carbinol (p. 77). 



To be added to synthetical pro- 

 cesses : 



[B, p. 77.] Butyramide and magne- 

 sium methiodide interact to form a com- 

 pound which is decomposed by water 

 into methylpropyl ketone (Be"is, Comp. 

 Rend. 137, 575). 



[E, p. 78.] Propionic acid and ethyl 

 alcohol [14] also yield diethyl ketone 

 by the interaction of propionamide and 

 magnesium ethobromide, and decom- 

 position of the product with water 

 (Beis, loc. cit.}. 



when mixed with hydrogen and passed 

 over reduced nickel at 135-165, gives 

 isoamyl alcohol by catalytic reduction 

 (Sabatier and Senderens, Comp. Rend. 

 137, 301). 



[C, p. 80.] From methyl and ethyl 

 alcohols [13; 14] and tartaric acid 

 [Vol. II]. The latter is converted into 

 pyroracemic (pyruvic) acid (see under 

 benzyl alcohol [54; N, p. 114]), and 

 the ethyl ester of the latter allowed to 

 interact with magnesium methiodide, 

 when isoamyl a-hydroxyisobutyrate is 

 formed (Grignard, Comp. Rend. 135, 

 627). The alcohol could be obtained 

 from its ester by hydrolysis. 



NOTE : Generators of pyroracemic acid other 

 than tartaric acid are available for this 

 synthesis. 



24. Isohexyl Alcohol (p. 82). 



To be added to synthetical pro- 

 cesses : 



[C, p. 82.] From ethyl and Isobutyl 

 alcohols [14 ; 18] and acetoacetic ester 

 [Vol. IIJ. Ethyl isobutyl-acetoacetate 

 on reduction in alcoholic solution with 

 sodium gives isohexyl alcohol (Bou- 

 veault and Blanc, Comp. Rend. 137, 

 328). 



25. Active Hexyl Alcohol (p. 83). 



Further confirmation of the presence 

 of this alcohol in Roman oil of chamo- 

 mile is given by Blaise, Bull. Soc. [3] 

 29, 327. 



22. Isoamyl Alcohol (p. 79). 



For occurrence of isoamyl alcohol in 

 Roman oil of chamomile see further 

 Blaise, Bull. Soc. [3] 29, 327. An 

 amyl alcohol (probably isoamyl) has 

 been found in oil of lavender (Schim- 

 mel's Ber. April, 1903 ; Ch. Centr. 

 1903, 1, 1086). 



To be added to synthetical pro- 

 cesses : 



[A, p. 80.] Isovaleric aldehyde vapour, 



27. Isoheptyl Alcohol (p. 83). 



To be added to synthetical pro- 

 cesses : 



[A, p. 83.] Or from ethyl alcohol 

 through ethylene oxide [92; A, p. 175] 

 and isoamyl magnesium bromide. The 

 latter interacts with ethylene oxide in 

 ethereal solution to form a compound 

 which gives isoheptyl alcohol on steam 

 distillation (Grignard, Comp. Rend. 

 136, 1260). 



