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# c12) United States Patent 

# Lambrecht et al. 

# (54) PROCESS FOR THE PREPARATION OF 1-HYDROPEROXY-16-OXABICYCLO [10.4.0]HEXADECANE 

(75) Inventors: Stefan Lambrecht, Holzminden (DE); Werner Marks, Breviirde (DE); Hans-Juergen Topp, Holzminden (DE); Norbert Richter, Beverungen (DE); Walter Kuhn, Holzminden (DE) 

(73) Assignee: symrise GmbH & Co. KG, Holmzinden (DE) 

( *) Notice: Subject to any disclaimer, the term of this patent is extended or adjusted under 35 U.S.C. 154(b) by O days. 

(21) Appl. No.: 10/939,012 

(22) Filed: Sep. 10, 2004 

## (65) Prior Publication Data 

US 2005/0085536 Al Apr. 21, 2005 

## (30) Foreign Application Priority Data 

Oct. 16, 2003 (DE) ................................ 103 48 168 

(51) Int. Cl. C07D 311/94 (2006.01) C07D 313/00 (2006.01) A61Q 13/00 (2006.01) 

(52) U.S. Cl. ....................................... 549/266; 549/396 

(58) Field of Classification Search ................ 549/266, 549/396 See application file for complete search history. 

<img src='content_image/947704.jpg'>

# (IO) Patent No.: US 7,098,347 B2 

# Aug. 29, 2006 (45) Date of Patent: 

## (56) References Cited 

<img src='content_image/947691.jpg'>

## FOREIGN PATENT DOCUMENTS 

<img src='content_image/947693.jpg'>

Chemical Abstracts 55:141087 (1961).* 

Roempp: "Chemie Lexicon, 10. Auflage" 1998, Georg Thieme Verlag, Stuttgart, DE, XP002318781. 

* cited by examiner 

Primary Examiner-Bernard Dentz 

(74) Attorney, Agent, or Firm-Akerman Senterfitt; Stephan A. Pendorf 

## (57) ABSTRACT 

Process for the preparation of l-hydroperoxy-16-oxabicyclo [10.4.0]hexadecane (DDP-OOH), wherein 13-oxabicyclo [10.4.0]hexadec-l (12)-ene (DDP) and hydrogen peroxide are reacted in a diluent in the presence of a strong acid, the diluent has a pKa value of greater than or equal to 4.5 and the strong acid has a pKa value of less than or equal to 1.5, wherein after the reaction has taken place, the strong acid is neutralized with at least 0.9 molar equivalent of a base. 

US00709834 7B2 

## U.S. PATENT DOCUMENTS 

## OTHER PUBLICATIONS 

## 18 Claims, No Drawings 

