Aug. 29, 2006  (45)  Date of Patent:  (IO)  Patent No.:  US 7,098,347 B2  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.  (56)  References Cited  U.S. PATENT DOCUMENTS  3,856,815 A  3,890,353 A *  5,266,559 A  12/1974 Hopp  6/1975 Becker ....................... 549/266  11/1993 Fankhauser  2004/0030194 Al  2/2004 Esser  FOREIGN PATENT DOCUMENTS  EP  EP  0 424 787 A  1 375 491 Al  5/1991  1/2004  OTHER PUBLICATIONS  * cited by examiner  Chemical Abstracts 55:141087 (1961).*  Roempp: "Chemie Lexicon, 10. Auflage" 1998, Georg Thieme  Verlag, Stuttgart, DE, XP002318781.  Primary Examiner-Bernard  Dentz  (74)  Attorney, Agent, or Firm-Akerman  Senterfitt; Stephan  A. Pendorf  (57)  ABSTRACT  18 Claims, No Drawings  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 