919. HAGEMEYER, H. J. (Eastman Kodak Co.). Ketene Condensation Products With Aldehydes. United States Patent 2,466,420, Apr. 5, 1949. Chem. Abs., vol. 43, 1949, p. 5037.

Patent Abstracts

Ketene (I) (2 mols.) is slowly added to Ni butyrate 1 gm. in furfural 200 cc. with high-speed stirring; the exothermic reaction keeps the mixture at 30º-40º. The reaction mixture contains mostly β-2-furyl-β-propional-acetone, as shown by distillation at 1 atm. with decarboxylation and formation of 30 gm. 2-vinylfuran (II). Ba(OAc)₂ at 45º gave 34 gm. (II), Co isobutyrate 34 gm. (II), and Zu butyrate 27 gm. (II). Yields of (II) without catalyst and outside the temperature range 30º-60º were low. Passage of (I) 84 into Hg (OAc)₂ 2 gm, in BzH 200 cc. at 45º gave mostly β-phenyl-β-propionolactone, converted by 30 min. reflux and distillation to 41 gm. styrene, b. 143º-144º. Other β-propionolactones prepared are the m-nitrophenyl, 5-methyl-2-furyl, 5-chloro-2furyl, 2-naphthyl, and p-propylphenyl derivatives.