Process for chlorinating tertiary alcohols

Abstract

The present invention relates to a process for converting a tertiary OH group of an organic compound into a tertiary C1 group of the organic compound by using a solvent selected from the group comprising toluene, o-xylene, m-xylene, p-xylene and mixtures thereof, and thionyl chloride as the chlorinating agent.

1 . A process for converting a tertiary OH group of an organic compound into a tertiary C1 group of the organic compound, said process comprising the steps of: 
 suspending or dissolving the tertiary alcohol in a solvent selected from the group consisting of toluene, o-xylene, m-xylene, p-xylene and mixtures thereof;    adding thionyl chloride to the resultant suspension or solution to form a reaction mixture without the presence of any catalyst in the reaction mixture, and separating the resultant organic compound comprising the tertiary C1 group from the reaction mixture.    
   
   
       2 . A process according to  claim 1 , wherein the step of separating the organic compound comprising the tertiary C1 group involves distillation of the reaction mixture.  
   
   
       3 . A process according to  claim 1 , wherein the organic compound comprising the tertiary C1 group is obtained as a solid after the reaction has taken place by cooling to below ambient temperature and drying at temperatures between 35° C. and 75° C.  
   
   
       4 . A process according to  claim 3 , wherein the drying step is performed under vacuum.  
   
   
       5 . A process according to  claim 1 , wherein the solvent is toluene.  
   
   
       6 . A process according to  claim 1 , wherein 1 to 2 equivalents of thionyl chloride, based on the amount of the tertiary alcohol, are added.  
   
   
       7 . A process according to  claim 6 , wherein 1.5 to 1.7 equivalents of thionyl chloride, based on the amount of the tertiary alcohol, are added.  
   
   
       8 . A process according to  claim 6 , wherein 1.6 equivalents of thionyl chloride, based on the amount of the tertiary alcohol, are added.  
   
   
       9 . A process according to  claim 1 , wherein a reaction is carried out with thionyl chloride at a temperature of 30 to 50° C.  
   
   
       10 . A process according to  claim 1 , wherein a reaction is carried out with thionyl chloride at a temperature of 35 to 45° C.  
   
   
       11 . A process according to  claim 1 , wherein a reaction is carried out with thionyl chloride for 1 to 4 hours.  
   
   
       12 . A process according to  claim 1 , wherein a reaction is carried out with thionyl chloride for 2 to 3 hours.