Yoshiyuki Tanaka, Jun P. Takahara, H. Lempers
Mar 18, 2009
Citations
0
Influential Citations
7
Citations
Journal
Organic Process Research & Development
Abstract
A selective synthesis of 3,3-dimethoxy methyl propionate has been developed using a green approach, in which the key step is a palladium-catalyzed oxidation of methylacrylate in methanol using oxygen as oxidant. The relationship between several reaction parameters including catalyst composition, oxygen pressure, substrate/solvent ratio, reaction temperature and reaction performance have been discussed. The data obtained in combination with data on explosion limits enabled successful scale-up to a 2 L scale, giving the desired product in 82% yield and 99% purity. Special attention is paid to catalyst activity, catalyst cost contribution, solvent recovery and safety. The product is a valuable industrial fine chemical for the synthesis of pharmaceuticals, functionalized polymers and adhesives, as it contains a protected aldehyde functional group, an ester functional group and an activated methylene function.