50 C-E.] 



ERYTHRITOL 



101 



N[CH 3 ] 2 ) by distilling the methiodide 

 with potassium hydroxide, and dimethyl- 

 pyrrolidine-methiodide (trimethylpyrro- 

 lidine iodide; C 4 H 7 . N[CH 3 ] 3 I) by 

 addition of methyl iodide. The latter 

 compound on distillation with caustic 

 alkali gives (among other products) 

 pyrrolylene or erythrene, which can be 

 treated as under A (Ciamician and 

 Magnaghi, Ber. 18, 2081; 19, 569; 

 Gazz. 15, 504). 



Or the succinimide can be converted 

 into dichlormalei'nimide by the action 

 of chlorine at 160 (Ciamician and 

 Silber, Ber. 16, 2393), perchlorpyrrole 

 chloride by the action of phosphorus 

 pentachloride, reduction to tetrachlor- 

 pyrrole with zinc dust and acetic acid, 

 conversion into tetraiodopyrrole by heat- 

 ing with potassium iodide solution, and 

 reduction to pyrrole with zinc dust in 

 alkaline solution (Ibid. 17, 554; 19? 

 3027), and then through N-methyl- 

 pyrrole, &c., as above. 



Also from succinic acid through 

 methylsuccinimide by distilling the 

 wetkylamme [Vol. II] salt (Menschut- 

 kin, Ann. 182, 92), conversion into 

 N-methylpyrrole by distilling with zinc 

 dust, and then as above. 



Or indirectly from succinic acid 

 through Isevulic acid by heating with 

 acetic anhydride (Fittig, Ber. 3O, 

 2148). From Isevulic acid through 

 N-methylpyrrole, &c., as below under D. 



Or succinic acid is converted into the 

 anhydride by heating with acetyl 

 chloride, the anhydride into rnono- 

 p < dium ethyl ester by treatment with 

 sodium ethoxide in alcoholic solution, 

 and the ester into succinoyl-ester 

 chloride (carbethoxypropionyl chloride) 

 by the action of phosphorus trichloride. 

 The chloride on treatment with zinc 

 methyl in benzene solution and decom- 

 position of the product with water 

 gives ethyl Isevulate, from which the 

 acid can be obtained by hydrolysis 

 (Blaise, Bull. Soc. [3] 21, 641 ; 647). 

 From Isevulic acid as below under D. 



Succinic ester and methylethyl ketone 

 (from acetic and propiomc acids] con- 

 dense under the influence of sodium 

 ethoxide to form y-ethylidene-y-methyl- 

 pyrotartaric acid (CH 3 . CH : C[CH 3 ] . 



CH[COOH] . CH 2 . COOH), which 

 gives Isevulic acid on oxidation with 

 potassium permanganate (Stobbe, Stri- 

 gel, and Meyer, Ann. 321, 105). 



[D.] From ethyl alcohol [14] and 

 acetic acid [Vol. II] by converting the 

 latter into chloracetic ethyl ester 

 (Willm, Ann. Chim. [3] 49, 97 ; Ann. 

 102, 109; Conrad, Ann. 188, 218), 

 and then into acetylsuccinic ester by 

 the interaction of chloracetic ester and 

 sodio-acetoacetic ester (Conrad, loc. cit.; 

 Rach, Ann. 234, 36). Acetylsuccinic 

 ester on boiling with dilute hydro- 

 chloric acid is converted into /3-acetyl- 

 propionic or Isevulic (4-pentanonic) acid 

 (Conrad, Ann. 188, 222; Ber. 11, 2177), 

 the oxime of which (y-isonitrosovalerie 

 acid) is formed by the action of hydr- 

 oxylamine on the ketonic acid (Miiller, 

 Ber. 16, 1618; Rischbieth, Ber. 2O, 

 2670). The oxime on heating with 

 sulphuric acid forms methylsuccinamie 

 acid (Bredt and Boddinghaus, Ann. 

 251, 319), and the latter on heating 

 gives methylsuccinimide (Ibid. 320), 

 from which N-methylpyrrole can be 

 obtained by heating with zinc dust as 

 under C. 



Or sodio-acetoacetic ester and ethyl- 

 ene bromide interact to form brom- 

 ethylacetoacetic ester, which on heating 

 with dilute hydrochloric acid gives 

 acetyl propyl alcohol. The latter gives 

 Iffivulic acid on oxidation with chromic 

 acid mixture (Lipp, Ber. 22, 1197). 



Divinyl is among the products 

 formed by passing the vapour of ethyl 

 alcohol over aluminium powder heated 

 to 580-680 (Ipatieff, Journ. pr. Ch. [2] 

 67, 420). 



[E.] From isoTiexoic add [Vol. II] by 

 long boiling with dilute nitric acid, 

 which gives the anhydride. of a-methyl- 

 hydroxyglutaric acid = 2 : 2-methylpen- 

 tanoldiacid (Bredt, Ber. 14, 1781). 

 This anhydride on heating with sul- 

 phuric acid gives Isevulic acid (Tollens 

 and Block, Ber. 19, 707), which can be 

 treated as under D. 



The anhydride can also be obtained 

 from isohexoic (isobiitylacetic) acid 

 through the anhydride of y-hydroxyiso- 

 hexoic acid by oxidising the former acid 

 with potassium permanganate (Bredt, 



