16 G-O.] 



ISOPROPYL ALCOHOL 



67 



[G.] From glycerol [48] through 

 propane (15 ; E) and then as above 

 through propyl and propylene chlorides, 

 &c. Or from glycerol through allyl 

 iodide (see under isobutyl alcohol [18 ; 

 D]) and propylene; or through allyl 

 alcohol and propylene (see under ace- 

 tone [106 ; F]). Or from glycerol 

 through allyl bromide (15 ; E). The 

 latter gives propylene on heating the 

 alcoholic solution with zinc dust (Wol- 

 koff and Menschutkin, Ber. 81, 3072 ; 

 Journ. Russ. Soc. 30, 559). Or allyl 

 bromide can be converted into tri- 

 methylene (15 ; E), and this yields pro- 

 pylene when heated to 600 (Tanatar, 

 Zeit. physik. Ch. 41, 735 : see also Ber. 

 32, 702 ; 1965). 



Glycerol gives propylene among the 

 products obtained by distilling it with 

 iodine and phosphorus (Berthelot and 

 De Luca, Ann. 92, 306 ; Ann. Chim. 

 [3] 44, 350 ; Oppenheim, Ann. Suppl. 

 6, 354), or with zinc dust (Westphal, 

 Ber. 18, 2931). 



From glycerol through isopropyl 

 iodide by distilling with iodine and 

 phosphorus in presence of water (Erlen- 

 meyer, Ann. 126, 305; 139, 21 1; 

 Markownikoff, Ann. 138, 364; Meyer, 

 Journ. pr. Ch. [2] 34, 98), and then as 

 above under B. 



Or from glycerol through dichlor- 

 hydrin by the action of hydrochloric 

 acid (Berthelot, Ann. Chim. [3] 41, 

 297 ; Reboul, Ann. Suppl. 1, 222 ; 

 Carius, Ann. 122, 73 ; Hiibner and 

 Miiller, Zeit. [2] 6, 344 ; Watt, Ber. 

 5, 257 ; Glaus, Kolver, and Nahm- 

 macher, Ann. 168, 43 ; Markownikoff, 

 Ann. 208, 358 ; Fauconnier and San- 

 son, Bull. Soc. [2] 48, 236 ; Fauconnier, 

 Ibid. 50, 212; Bigot, Ann. Chim. [6] 

 22, 437). Dichlorhydrin gives iso- 

 propyl alcohol among the products of 

 reduction by sodium amalgam (Buff, 

 Ann. Suppl. 5, 250). 



Or (indirectly) dichlorhydrin can be 

 converted into I : 2 : 3-trichlorpropane 

 (Berthelot and De Luca, Ann. Chim. 

 [3] 48, 304; 52, 433; Fittig and 

 Pfeffer, Ann. 135, 359), a-chlorallyl 

 chloride (CH 2 : CC1. CH. 2 C1) by the 

 action of potash or triethylamine (Re- 

 boul, Ann. Suppl. 1, 229 ; Comp. Rend. 



95, 993), a-chlorallyl alcohol by heating 

 with aqueous potassium carbonate, and 

 then through aceiyl carbinol, &c., as above 

 under A. 



[H.] From erythritol [50] through 

 2-iodobutane and propane (15 ; P). 



[I.] From mannitol [5l] through 

 2-iodohexane and propane or through 

 acrole'in [lOl], acrylic acid, &c., to pyro- 

 tartaric acid (15 ; G) and then as above 

 under A. 



Or from mannitol through n-hexane 

 (see under n-hexyl alcohol [23 ; B] and 

 n-propyl alcohol [15 ; Gj). Propylene 

 is formed among other products by 

 passing u-hexane mixed with air over 

 heated platinum (v. Stepski, Monats. 

 23, 773)- 



NOTE : All generators of n-hexane given 

 under n-hexyl alcohol [23], viz. n-propyl alcohol 

 [15] ; glycerol [48] ; suberic acid [Vol. II] ; acetone 

 [106], &c. ,thus become generators, through pro- 

 pylene, of isopropyl alcohol. 



[J.] Thymol [67] gives propylene on 

 heating with phosphorus pentoxide 

 (Engelhardt and Latschinoff, Zeit. [2] 

 5, 6 1 6). Or from thymol through 

 thymoquinone to succinylsuccinic acid 

 (ester) and ethylmalonic acid as under n- 

 propyl alcohol (15; O; Y; BB). Ethyl- 

 malonic acid gives isopropyl alcohol 

 among the products of electrolysis of 

 the solution of the potassium salt 

 (Petersen, Zeit. physik. Ch. 33, 698; 

 Ch. Centr. 1900, 2, 172). 



[K.] From carvacrol [66] through 

 thymoquinone, &c. (15 ; CC), and then 

 as above. 



[L.] From aldehyde [92] through 

 butyrochloral to acrylic and pyrotar- 

 taric acids (15 ; J). From the latter 

 as above under A. Or from aldehyde 

 and methyl alcohol by the interaction 

 of magnesium methiodide and the alde- 

 hyde (Grignard, Ch. Centr. 1901, 2, 

 622). 



[M.] From acrole'in [lOl] through 

 acrylic to pyrotartaric acid (15 ; E). 



[N.] From crotonic aldehyde [102] 

 through crotonic acid to pyrotartaric 

 acid, or through a-brombutyric acid, 

 nitropropane, and n-propylamine (15; 

 I). From the latter as above under C. 



[O.] From acetyl carlinol [43] as above 

 under A. 



