31335-17-8Relevant academic research and scientific papers
Synthesis of diketones and ω-hydroxy ketones from methyl ketones and α,ω-diols by an [IrCl(eod)]2/PPh3/KOH system
Maeda, Kensaku,Obora, Yasushi,Sakaguchi, Satoshi,Ishii, Yasutaka
experimental part, p. 689 - 696 (2009/04/07)
ω-Hydroxy ketones and diketones, which are important starting materials for the synthesis of cycloalkanones and heterocyclic compounds, were prepared by the one-step reaction of methyl ketones with α,ω-diols under the influence of an iridium complex and a base. The selectivity of ω-hydroxy ketones and diketones could be controlled by varying the starting ratio of methyl ketones to α,ωdiols. For example, reaction using acetophenone (5 equiv) with respect to 1,6-hexanediol (1 equiv) in the presence of [IrCl(cod)]2, PPh3, and KOH without solvent gave 1,10-diphenyl-1,10-decane-dione in almost quantitative yield, while reaction using acetophenone (1 equiv) to 1,6-hexanediol (4 equiv) led to 8-hy-droxy-l-phenyl-l-octanone in 92% yield. This methodology was successfully extended to the reaction of arylacetonitriles with α.ω-odiols leading to diaryldinitriles.
