Process for the production of 3-alky-3-hydroxymethyloxetanes

US6166228A · kind A · utility

Assignee

• Dainippon Ink and Chemicals, Inc. · JP

Inventors

• Kai-Uwe Gaudl · Wantage, US
• Artur Lachowicz · Berlin, DE
• Andreas Hoffmann · North Bend, US
• Gerwald Grahe · Berlin, DE

Key dates

• Filing date: Mar 17, 2000
• Grant date: Dec 26, 2000
• Expiry date: Mar 17, 2020

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D305/06
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A process is described for the production of 3-alkyl-3-hydroxymethyloxetanes of the general formula (1), ##STR1## in which R.sup.1 denotes a linear or branched C.sub.1 -C.sub.12 alkyl group, which process comprises reacting a trimethylolalkane of the general formula (2), EQU (HO--CH.sub.2).sub.3 C--R.sup.1 (2) in which R.sup.1 is defined as above, with a dialkyl carbonate of the general formula (3), EQU R.sup.2 --O--(C.dbd.O)--O--R.sup.2 (3) in which R.sup.2 denotes a linear or branched C.sub.1 -C.sub.4 alkyl group, in the presence of a basic catalyst, wherein in a first stage the reaction mixture is stirred for at least 6 hours with refluxing at a temperature of 90-120.degree. C., in a second stage the alcohol formed R.sub.2 OH is distilled off at the same temperature and in a third stage the product formed is decarboxylated and deoligomerised at a temperature of 125-150.degree. C. and the desired 3-alkyl-3-hydroxymethyloxetane is simultaneously distilled off.