公开(公告)号：US3565915A

公开(公告)日：1971-02-23

申请号：US3565915D

申请日：1966-05-24

Applicant: SUMITOMO CHEMICAL CO

Inventor： MATSUI MASANAO ,  YOSHIOKA HIROSUKE ,  SAKAMOTO HIDEO ,  YAMADA YASUHIRO

IPC: C07C45/66 ,  C07C49/553 ,  C07C61/04 ,  C07D7/06

CPC classification number: C07C61/04 ,  C07C45/66 ,  C07C49/553

Abstract: A PROCESS IS PROVIDED FOR PRODUCING AN OPTICALLY ACTIVE DIHYDROCHRYSANTHEMOLACTONE REPRESENTED BY THE FOLLOWING FORMULA:

4,4,7,7-TETRA(CH3-)-3-OXABICYCLO(4.1.O)HEPTAN-2-ONE

WHICH IS USEFUL IN THE PRODUCTION OF INSECTICIDES. THE PROCESS COMPRISES TREATING OPTICALLY ACTIVE 2,2-DIMETHYL3-CIS-(2''-OXO) PROPYL-CYCLO-PROPYL - 1 - ACETALDEHYDE IN AN AQUEOUS ALKALINE OR ACID SOLUTION OR ACETIC ACID ANHYDRIDE, OR IN AN ORGANIC SOLVENT WITH USE OF CATALYST, AT A TEMPERATURE OF 50* TO 200*C., REACTING THE RESULTING OPTICALLY ACTIVE 2-ACETYL-6,6-DIMETHYL-BICYCLO(3,1,0)-2-HEXENE WITH OZONE GAS IN AN ORGANIC SOLVENT AT A TEMPERATURE OF -60* TO 20*C., TREATING THE RESULTING OZONIDE WITH HYDROGEN PEROXIDE, PERIODIC ACID OR ITS SALT AND TREATING THE RESULTING CIS-HOMOCARONIC ACID IN EXCESS ACETIC ACID ANHYDRIDE AT A TEMPERATURE OF 100* TO 150*C. TO FORM OPTICALLY ACTIVE CIS-HOMOCARONIC ACID ANHYDRIDE AND TREATING SAID ANHYDRIDE WITH A GRIGNARD REAGENT REPRESENTED BY THE FORMULA CH3MGX WHERE X IS HALOGEN.