Production of alkoxy phenolic compounds

Abstract

Alkoxy phenols such as o-methoxyphenol (guaiacol) and o-ethoxyphenol are prepared from substituted cycloaliphatic ketones by dehydrogenation thereof in the presence of a Group VIII noble metal catalyst, preferably palladium supported on carbon, at a temperature of 150° C., to 250° C. The reaction is carried out neat or in the liquid phase using an alicyclic ester reaction solvent having a boiling point ranging from about 150° C., to 250° C. The substituted cycloaliphatic ketone reactant, such as 2-chlorocyclohexanone is prepared by chlorination of cyclohexanone with subsequent conversion of the 2-chlorocyclohexanone to the alkoxy-cyclohexanone compound which is dehydrogenated.

The embodiments of the invention in which a particular property or privilege is claimed are defined as follows: .[.1. The process for the preparation of an o-alkoxyphenol in high yield and selectivity, comprising: 
     
        superatmospheric pressure..]. 11. The process for the preparation of an o-alkoxyphenol selected from the group consisting of o-methoxyphenol and o-ethoxyphenol, comprising: refluxing an alkoxycyclohexanone selected from the group consisting of 2-methoxycyclohexanone and 2-ethoxycyclohexanone substantially in the absence of a solvent for the alkoxycyclohexanone together with a Group VIII noble metal catalyst at a temperature of from about 150° C. to 250° C., and   
     
     
       recovering the alkoxyphenol. 12. The process of claim 11 in which the catalyst is palladium supported on an inert carrier present in an amount ranging from 0.10 to 3.0 weight percent relative to the 
     
     
        alkoxycyclohexanone. 13. The process of claim 11 in which the process is 
     
     
        carried out at superatmospheric pressure. 14. The process of claim 11 in which the catalyst is palladium supported on an inert carrier and the reaction is refluxed at superatmospheric pressure.