ChemInform Abstract: REACTION OF 2,6‐DI‐TERT‐BUTYLPHENOL WITH METHYL ACRYLATE IN THE PRESENCE OF BASES

Abstract

Die Darstellung des Esters (I) aus 2,6‐Di‐tert.‐butylphenol und Methylacrylat (II) in Gegenwart von Alkalimetallen ist in der Patentliteratur beschrieben.

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

“…The NMR 1 H spectrum of the oligomer exhibits a narrow signal at δ = 3.62 from the protons of the MeO group and a signal at δ = 1.3 characteristic of the protons of the tertbutyl groups, which possibly indicate that an oligomer molecule contains the terminal phenol moiety. It is known [9] that the NMR 1 H spectrum of an analog of the oligomer, being the condensation product of 2,6-di-tert-butylphenol with three methyl acrylate molecules, contains signals of protons in the region characteristic of an oligomer with a higher content of the methyl acrylate fragments (n = 143). The reaction of phenoxide ArOK with methyl acrylate in the presence of MeOH at room temperature affords a methyl acrylate polymer insoluble in organic solvents.…”

Potassium and Sodium 2,6-Di-tert-Butyl Phenoxides and their Properties

“…It is also known that at room temperature 2,6-Bu t 2 C 6 H 3 OH does not react with alkaline metalhydroxides [6], whereas at 273-413 K the rate of this process is insufficient [7] for the preparation of 2,6-di-tert-butyl phenoxides in the individual form due to reversibility of the process. The studied reactions of 2,6-dialkyl phenoxides are described in the review [8] and publications [9][10][11][12][13] associated with the use of the corresponding phenoxides in the catalytic alkylation of 2,6-dialkylphenols. Despite the interest in alkylation of 2,6-Bu t 2 C 6 H 3 OH, the data on the properties of individual phenoxides are insufficient, scanty, and contradictory.…”