L-Chloro-2-propanone

Synonyms Monochloroacetone chloroprop-anone l-chloro-2-propanone acetonyl chloride... 

Nitrobromoform, Bromoacquinite, Tribromonitromethane, Picfume bromide Chloroacetone, l-Chloro-2-propanone Cyanogen, EthanedinitrUe, Dicyan, Oxalic acid dinitrUe, Dicyanide Chloroacetone, l-Chloro-2-propanone... 

Nitrobromoform, Bromoacquinite, Tribromonitromethane, Picfume bromide Chloroacetone, l-Chloro-2-propanone... 

In a hood, to a well-stirred dispersion of 62 gm (1.35 moles) of methyl-hydrazine, 175 ml of chlorobenzene, and 20 gm of powdered, anhydrous sodium sulfate is added dropwise, with cooling, 61 gm (0.663 mole) of freshly distilled l-chloro-2-propanone. After the addition has been completed, the reaction mixture is stirred for 1 hr. The moist sodium sulfate is separated by filtration and the filtrate is distilled. The fraction boiling between 60°C and 64°C is collected as product, yield 16.8 gm (31 %) of a yellow liquid. On redistillation the boiling point is raised slightly to 61°-64°C, index 1.4300. 

CtHfiCIO CiHiO l-Chloro-2-propanone Isopropyl alcohol 119.7 82.4 Nonazeotrope 686... 

The saccharinic acid was next prepared in 32 % yield from the halogen acid (XLIII) by treatment with silver oxide, but this approach was abandoned when good results were obtained from the acetol-form-ester. Reaction of l-chloro-2-propanone (XLVII) with sodium formate produced the monoformate of l-hydroxy-2-propanone (XLIX) which, through the addition of hydrogen cyanide and hydrolysis of the resulting cyanohydrin of l-hydroxy-2-propanone (L), yielded the desired racemic saccharinic acid (Vab). 

Vitzthum and Werkhoff (1974a) confirmed the structure of the product using the synthesis according to Theilig (1953) by reaction of acetol acetate with ammonia. The compound was previously synthesized by Lewy (1888) by the reaction of l-chloro-2-propanone (chloroacetone) with acetamide. The same procedure was used by Zinsstag and Prijs (1949). 

As in lutidine-methanol, l-chloro-2-propanone undergoes methanolysis much more slowly than does 29c this difference in reactivity is due to the effect of the two phenyl groups in zwitterion 32. ... 

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