Syntheses based on 2-hydroxyacetophenone

US5696274A · kind A · utility

Assignee

• Hoechst Celanese Corporation · US

Inventors

• Ibrahim M. Uwaydah · Port Aransas, US
• Mohammad Aslam · Port Aransas, US
• Charles H. Brown, II · Fresno Street, US
• Sharon R. Fitzhenry · Foxborough, US
• Joseph A. McDonough · Port Aransas, US

Key dates

• Filing date: May 22, 1996
• Grant date: Dec 9, 1997
• Expiry date: May 22, 2016

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D311/56
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention provides processes which are flexible, cost effective, and commercially viable methods of manufacturing or producing products from 2-hydroxyacetophenone (2-HAP). Of particular interest of the available products are 4-hydroxycoumarin, warfarin-alkali salt, preferably warfarin sodium and warfarin-alkali salt-isopropyl alcohol (2-propanol) complex, more preferably warfarin-sodium-isopropyl alcohol complex. As is known, these compounds are useful as vitamin K dependent anticoagulants in the treatment of humans and animals. In different doses, they are also useful as rodenticide. The inventive process involves contacting 2-HAP, carbonate ester and effective base followed by treatment with an unsaturated ketone and phase transfer catalyst to ultimately yield product.