Preparation of 13-oxabicyclo[10.3.0]pentadecane

US4360468A · kind A · utility

Assignee

• Henkel Kommanditgesellschaft auf Aktien · DE

Inventors

• Horst Upadek · Erkrath, DE
• Klaus Bruns · Uerdingen, DE

Key dates

• Filing date: Sep 29, 1981
• Grant date: Nov 23, 1982
• Expiry date: Sep 29, 2001

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D307/93
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

This invention relates to the preparation of 13-oxabicyclo[10.3.0]pentadecane. More specifically, this invention relates to a process for preparing 13-oxabicyclo[10.3.0]pentadecane which comprises the steps of: PA0 (a) reacting cyclododecanone with elemental bromine in an organic solvent to form .alpha.-bromocyclododecanone; PA0 (b) reacting .alpha.-bromocyclododecanone with malonic acid dialkyl ester and alkali metal alcoholate to form the ketodiester 2-(2-oxocyclododec-1-yl)-malonic acid dialkyl ester; PA0 (c) hydrolyzing and decarboxylating the ketodiester from step (b) to from the corresponding 2-oxocyclododec-1-yl-acetic acid in an aqueous alkaline solution; PA0 (d) purifying the product of step (c) by extraction with an organic solvent and obtaining 2-oxocyclododec-1-yl-acetic acid; PA0 (e) reacting the product of step (d) with a lower alcohol to form a corresponding ester; PA0 (f) reducing the product of step (e) with a complex metallic hydride to form 2-(2-hydroxyethyl)-cyclododecanol; and PA0 (g) heating the product of step (f) in the presence of an acid catalyst to form 13-oxabicyclo[10.3.0]pentadecane.