Synthesis of 2,2,6,6-tetrahydroxymethyl cyclohexanol allyl ether

2,2,6,6-tetramethylolcyclohexanol(TMC) has been synthesized by consecutive aldol condensation and Cannizzaro reactions of cyclohexanone and formaldehyde with an alkaline catalyst.2,2,6,6-tetramethylol cyclohexanol allyl ether(TMAE) was subsequently prepared by reaction of TMC with allyl chloride using tetrabutylammonium bromide as phase transfer catalyst.The chemical structures of the products were confirmed by FT-IR,1H NMR,and 13C NMR spectroscopies. The effects of varying the temperature,the amount of catalyst,and the molar ratio of reactants on the yield of TMAE were investigated.A 58.3% yield of TMAE was obtained by using the optimal reaction conditions as follows: n(alkali)∶n(formaldehyde)∶n(cyclohexanone) of 1.25∶5.5∶1,aldol condensation temperature of 10 ℃ and time of 1 hour,Cannizzaro reaction temperature of 40 ℃ and time of 1.5 hours,n(sodium hydroxide)∶n(allyl chloride)∶n(TMC) of 9∶10∶1,weight of TBAB being 10% of that of TMC,reaction temperature of 80 ℃ and time of 120 hours.