Cyclodecanone reduction

The procedure described is a modification of the directions of Prelog, Frenkiel, Kobelt, and Barman. Cyclodecanone has been prepared by the dehydration of sebacoin followed by catalytic hydrogenation, by the pyrolysis of the thorium or yttrium salt of nonane-1,9-dicarboxylie acid, and by the ring enlargement of cyclononanone, as well as by the reduction of sebacoin. ... 

Cyclodecanone has been obtained together with other products in the pyrolysis of the thorium or yttrium salts of nonanedioic acid.3 4 It has also been prepared by reduction of sebacoin with zinc and hydrochloric acid,6, 6 by dehydration of sebacoin fol-... 

The overall yield of cyclodecanone is comparable to the overall yield obtained by conversion of dimethyl sebacate to sebacoin 11 and subsequent reduction to cyclodecanone.6 In addition, the present procedure does not require the use of a high-speed stirrer, the rigorous exclusion of air, and the high dilution that are necessary in preparing sebacoin. 

I 14. Oxidation of cyclodecanol to cyclodecanone is rapid with Cr03 in acid but reduction of cyclodecanone to... 

Zinc is the classical reagent for removing a ketone carbonyl via reaction with zinc amalgam (Zn/Hg) in HCl, the Clemmensen reduction. lO Reduction of ketone 534 to 535 is an example of this conversion. The effectiveness of using zinc in acid for reduction is seen in the removal of a hydroxyl group from an acyloin such as 536 (sec. 13.8.E) to give cyclodecanone, 537.5 2 a useful modification of this reaction was... 

---