Metal-catalyzed alkoxycarbonylation of a lactone

US10519094B2 · kind B2 · utility

Assignee

• QATAR FOUNDATION FOR EDUCATION, SCIENCE AND COMMUNITY DEVELOPMENT · QA

Inventors

• Sarim Dastgir · Doha, QA
• Muhammed Sharif · Rostock, DE
• Ralf Jackstell · Rostock, DE
• Matthias Beller · Ostseebad Nienhagen, DE
• Francesco Ferretti · Doha, QA

Key dates

• Filing date: Mar 19, 2018
• Grant date: Dec 31, 2019
• Expiry date: Mar 19, 2038

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C55/00
• WIPO field: Chemical engineering
• WIPO sector: Chemistry

Abstract

The metal-catalyzed alkoxycarbonylation of a lactone is a method of alkoxycarbonylating a δ-lactone, specifically 3-ethylidene-6-vinyltetrahydro-2H-pyran-2-one. The method includes combining the δ-lactone with an alcohol in an organic solvent in the presence of a catalyst system that includes palladium or a salt thereof to form a reaction mixture, which is heated to 110-130° C. at a pressure of 20-50 bar for between 3-5 hours under flow of carbon monoxide gas. The product of the reaction is a substituted 2-octendioate diester. The alcohol may be methyl alcohol, n-butyl alcohol, 2-ethylhexanol, isobutyl alcohol, isopropyl alcohol, benzyl alcohol, or phenol. The solvent may be toluene, acetonitrile, or tetrahydrofuran. The method may include adding an acid to the reaction mixture, which may be dilute (about 5 mol %) sulfuric or p-toluenesulfonic acid. The catalyst system may also include a phosphine ligand.