Alkylation of 2,6-di-tert-Butylphenol with Methyl Acrylate Catalyzed by Potassium 2,6-di-tert-Butylphenoxide

Authors: 
Gennady Zaikov and Alexander Volod’kin

The kinetics of catalytic alkylation of 2,6-di-tert-butylphenol (ArOH) with methyl acrylate (MA) in the presence of potassium 2,6-di-tert-butylphenoxide (ArOK) depends on the method for the preparation of ArOK. The reaction of ArOH with KOH at temperatures > 453 K affords monomeric ArOK, which properties differ from those in the case of potassium 2,6-di-tert-butylphenoxide synthesized by the earlier methods. The regularities of ArOH alkylation depend on the ArOK concentration, the ArOH:MA ratio, and the effect of microadditives of polar solvents.

[1] Volod’kin A., Paramonov V., Egidis F. and Popov L.: Khim. Promyshl., 1988, 12, 7.
[2] Ershov V., Nikiforov G. and Volod’kin A.: Prostranstvenno-zatrudnennye fenoly. Khimiya, Moskwa 1972.
[3] Volod’kin A., Zaitsev A., Rubailo V. et al.: Bull. Acad. Sci. USSR, 1989, 38, 1677.
[4] Volod’kin A.: Russ. Chem. Bull., 1994, 43, 769.
[5] Volod’kin A. and Zaikov G.: Russ. Chem. Bull., 2006, 55, 2212.
[6] Matilainen L., Leskela M. and Klinga M.: J. Chem. Soc., Chem. Commun., 1995, 421.
[7] Malysheva N., Prokof’ev F., Bubnov N. et al.: Izv. Akad. Nauk SSSR, Ser. Khim., 1977, 1522.
[8] Burton L.: US Pat. 4659863; Chem. Abstr., 1988, 107, 77439.
[9] Titova T., Krysin A., Bulgakov V. and Mamatyuk V.: Zh. Org. Khim., 1984, 20, 1899.