Isocaproyl chloride

The gas inlet tube is replaced by a dropping funnel protected by a calcium chloride drying tube. Isocaproyl chloride (84.7 g., 0.63 mole) (Note 5) is added to the reaction mixture with stirring over a period of 20 minutes. The dropping funnel is replaced by the gas inlet tube (inlet tube wiped with a dry towel), and, with stirring, acetylene is bubbled just below the surface of the mixture at a rate noticeably above the saturation rate. After 15 minutes to 1 hour the rate of absorption of acetylene suddenly becomes very rapid, and the acetylene is passed through as rapidly as it is absorbed (Note 6). The introduction of acetylene is continued for 30 minutes after the rapid absorption (which lasts 1-2 hours) has subsided. 

Eastman Kodak Company white label isocaproyl chloride was redistilled and the middle 80% portion was used. 

Isocaproyl chloride, 32, 27 ISOCYANIC ACID, HEXAMETHYLENE ESTER, 31, 62... 

The Leukart reaction has also been used in the conversion of dehydroepiandro-sterone into 17/3-formylamino-3/3-formyloxyandrost-5-ene, which on reduction with lithium aluminium hydride afforded 3/3-hydroxy-17/3-me thylaminoandrost-5-ene. Acylation with isocaproyl chloride then furnished the N-methyl-N-isocaproyl steroid (197), after selective ester hydrolysis of the initially formed ON-diacyl derivative. The amide (197) was further converted into its 3,5-cyclo-6-ketone via the 3,5-cyclo-6/3-alcohol and thence by reaction with hydrogen bromide into the corresponding 3/3-bromo-5a-6-ketone which upon dehydrobromination furnished a A2-5a-6-ketone and ultimately the 2-monoacetate of the 2/3,3/3-diol (198) after reaction with silver acetate and iodine. Hydrolysis to the 2/3,3/3-diol (198) gave a separable mixture of the 2/3,3/8-dihydroxy-5a- and -5/3-ketones.88... 

Addition of isocaproyl chloride to acetylene to produce /3-chlorovinyl isoamyl ketone is accomplished by saturating carbon tetrachloride with acetylene, adding... 

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