| 摘要 |
1,205,047. Preparation of cycloalkanones. R. FIRMENICH, G. FIRMENICH, R. E. FIRMENICH, and F. H. FIRMENICH, [trading as FIRMENICH & CIE]. 8 Dec., 1967 [8 Dec., 1966], No. 55866/67. Heading C2C. Cyclopentadecanone and 3 - methyl - cyclopentadecanone are prepared by catalytically hydrogenating an unsaturated ketone of formula wherein R is H or CH 3 and X is -CH 2 -CH= CH-, -CH = CH-CH 2 -, -CH 2 -C#C- or -C#C-CH 2 -. In examples: (1) a mixture of cyclopentadec-4- and -5-ene-1-ones is hydrogenated using H 2 and Raney nickel to give cyclopentadecenone; (2) 3-methylcyclopentadecan-1-one is prepared as in (1) from the corresponding unsaturated ketones and its semicarbazone is specified, (3) bicyclo[10.3.0]pentadec-1(12)-en-13-one is oxidized with H 2 O 2 to 1,12 - epoxy - bicyclo[10.3.0]pentadec - 13 - one which is treated with toluene-p-sulphonyl hydrazide to yield the corresponding tosylhydrazone which is decomposed by passage through a column of silica gel to give cyclopentadec-4-yn - 1 - one, which is successively hydrogenated to cis-cyclopentadec-4-en-1-one and cyclopentadecanone. Further examples are given.
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