Isobutyroyl chloride

Acyl radicals can fragment with toss of carbon monoxide. Decarbonylation is slower than decarboxylation, but the rate also depends on the stability of the radical that is formed. For example, when reaction of isobutyraldehyde with carbon tetrachloride is initiated by t-butyl peroxide, both isopropyl chloride and isobutyroyl chloride are formed. Decarbonylation is competitive with the chlorine-atom abstraction. 

Cyclohexanone 4-Toluenesulfonic acid Isobutyroyl chloride Methylamine... 

To solution of 16.7 g 1-morpholinocyclohex-l-ene in 45 ml chloroform, 10.1 g of triethylamine are added. Over a period of one hour a solution of 1 mole-equivalent of isobutyroyl chloride in 15 ml chloroform is added, with stirring. The mixture is stirred for two hours at room temperature and is thereafter heated at 60°C for 3 hours. It is kept aside for a night, then 150 ml hydrochloric acid are added. The mixture is shaken and is then allowed to settle. The chloroformic phase is discarded. The aqueous phase is partially neutralized with sodium carbonate until the pH value reaches 6 and is then extracted with chloroform three times. The organic phases are united, washed with water, dried over sodium sulfate, filtered and evaporated to dryness. The crude residue is purified by distillation under reduced pressure to give 2-(isobutyroyl)cyclohexanone. 

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