F Butyryl chloride

NaBH4 is superior to LiAlH4 in selective reductions. In "water or methanol soln., it is an effective reagent for the conversion of aldehydes and ketones to the corresponding alcohols. Aoid chlorides are reduced to prim, alcohols in non-aq. media, but carboxylic acids, anhydrides, esters and nitriles are practically unaffected.—E Cinnamaldehyde —> cinnamyl alcohol. Y 97%.—n-Butyryl chloride —n-butanol Y 81%. (F. e. s. S. W. Chaikin, W. G-. Brown, Am. Soc. 71,122 (1949) s. a. H. Heusser et al., Helv. 33, 1093 (1950).)... 

BUTYRYL CHLORIDE or -BUTYRYL CHLORIDE (141-75-3) Forms explosive mixture with air (flash point <70°F/<2l°C). Slowly reacts with moist air, water, steam, and alcohols, forming hydrogen chloride and phosgene gas. Violent reaction with strong oxidizers, strong bases. Corrodes metals in the presence of moisture. May accumulate static electrical charges may cause ignition of its vapors. 

Furfurylthio)butyryl chloride added gradually to benzene and SnCl4, then stirred 1-2 hrs. 5-ethyl-4,5-dihydro-7H-furo[2,3-c]thia-4-pyranone (Y 81%) heated 1.5-2 hrs. with Raney-Ni in acetone-ethanol propyl 2-methyl-3-furyl ketone (Y 53-55%). F. e. s. Y. L. Gol dfarb and L. D. Tarasova, Dokl. Akad. Nauk SSSR 142, 358 (1962) G. A. 57, 789c. 

A mixture of 4-hydroxy-5-methylfuran-2(5H)-one, butyryl chloride, XiCl4, and nitrobenzene warmed 2.5 hrs. at 50° with stirring 3-butyryl-4-hydroxy-5-meth-ylfuran-2(5H)-one. Y 72%. F. e. and limitations s. J. L. Bloomer and F. E. Kapp-ler, Soc. Perkin I 1976, 1485. 

A mixture of butyryl chloride and ethyl diazoacetate allowed to stand 10 days at room temp, in the presence of a few boiling stones ethyl butyryldiazo-acetate (Y 80%) dissolved with triphenylphosphine in abs. ether, which is then distilled off, the residue warmed 24 hrs. at 65° crude ethyl butyrylglyoxylate-2-triphenylphosphazine (Y 86%) dissolved in tetrahydrofuran free of 0x0 compounds, a little acetic acid added, then water added in 3 portions during 1 hr., allowed to stand 24 hrs. at room temp., the resulting crude hydrazone treated with N-methylpiperidine, a few boiling stones added, and warmed ca. 18 hrs. at 60° under anhydrous conditions until Ng-evolution ceases ethyl butyrylacetate (Y 77%).—Quinoline in abs. ethanol or pyridine may be used in place of N-methylpiperidine. F. e. s. H. J.Bestmann and H.Kolm, B. 96, 1948 (1963). 

An ethereal suspension of thallous benzoate (prepared from benzoic acid and thallous ethoxide) treated 6 hrs. at 25° with the stoichiometric amount of iso-butyryl chloride benzoic isobutyric anhydride. Y ca. 100%. - To minimize comproportionation, the carboxylate salt of the weaker acid should be used. F. e., also phenolesters and phenyl sulfonates with thallous phenoxides, as well as sym. carboxylic acid anhydrides from thallous carboxylates with SOCU, s. E. G. Taylor, G. W. McLay, and A. McKillop, Am. Soc. 90, 2422 (1968). 

Fluorosulfonic acid added drop wise with cooling and stirring at ca. —5° to n-butyric anhydride, and warmed slowly to room temp, under reduced pressure n-butyryl fluoride. Y ca. 95%. F. e., also carboxylic acid chlorides with chlorosulfonic acid, s. M. Schmidt and K. E. Pichl, B. 98, 1003 (1965). ... 

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