Preparation of α-hydroxy ketones via carbene-catalyzed umpolung reaction of aldehydes

US7504542B2 · kind B2 · utility

Assignee

• EVONIK DEGUSSA GMBH · DE

Inventors

• Ralf Jackstell · Rostock, DE
• Irina Jovel · Rostock, DE
• Matthias Beller · Ostseebad Nienhagen, DE
• Martin Hateley · Aschaffenburg, DE
• Christoph Weckbecker · Gelnhausen, DE
• Klaus Huthmacher · Gelnhausen, DE

Key dates

• Filing date: Aug 10, 2007
• Grant date: Mar 17, 2009
• Expiry date: Aug 10, 2027

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C2601/14
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention relates to the preparation of α-hydroxy ketones of the general formula I. In particular, the invention relates to novel imidazolinium carboxylate adducts and to a novel process for using catalytic amounts of imidazolium and imidazolinium carboxylate adducts in the acyloin reaction of aldehydes to prepare hydroxy ketones of the general formula I,where R and R′ are the same or different and are each H or a straight-chain or branched and optionally substituted C1-C12-alkyl radical, and R″═H3CSCH2CH2, t-butyl, n-butyl, sec-butyl, n-propyl, i-propyl, an optionally heteroatom-substituted C6-C18-aryl, heteroaryl, C6-C18-arylalkyl, especially phenylmethyl, where phenyl may again be heteroatom-substituted, or heteroalkyl.