Synthesis of omega-hydroxy carboxylic acids and alpha,omega-dimethyl ketones using alpha,omega-diols as alkylating agents.
Synthesis of omega-hydroxy carboxylic acids and alpha,omega-dimethyl diketones was successfully achieved by using alpha,omega-diols as alkylating agents under the influence of an iridium catalyst. For example, the alkylation of butyl cyanoacetate with 1,13-tridecanediol in the presence of [IrCl(cod)](2) or [IrCl(coe)(2)](2) gave rise to butyl 2-cyano-15-hydroxypentadecanoate in good yield which is easily converted to cyclopentadecanolide (CPDL). In addition, the alkylation of acetone with 1,10-decanediol in the presence of [IrCl(cod)](2) and KOH resulted in an important muscone precursor, 2,15-hexadecanedione (HDDO), in good yield.
Iuchi
Yosuke
Y
Department of Chemistry and Materials Engineering, Faculty of Chemistry, Materials and Bioengineering and High Technology Research Center, Kansai University, Suita, Osaka 564-8680, Japan.
Hyotanishi
Megumi
M
Miller
Brittany E
BE
Maeda
Kensaku
K
Obora
Yasushi
Y
Ishii
Yasutaka
Y