128203-42-9Relevant articles and documents
New opportunities for duff reaction
Belostotskaya,Komissarova,Prokof'Eva,Kurkovskaya,Vol'Eva
, p. 703 - 706 (2005)
Reaction of 2,4-di-tert-butylphenol with urotropin in conditions of Duff reaction takes an abnormal route and instead of the expected di-tert-butylsalicylaldehyde provides a mixture of N-substituted 3,5-di-tert-butyl-2-hydroxybenzylamines and redox conjugate benzoxazines containing mostly 6,8-di-tert-butyl-3-(3,5-di-tert-butyl-2-hydroxybenzyl)-2H-3, 4-dihydrobenz[e][1,3]oxazine. A solvolysis of an individual benzoxazine in the system HO(CH2)2OH-H2O-HCl affords di(3,5-di-tert-butyl-2-hydroxybenzyl)amine, and in AcOH 3,5-di-tert- butylsalicilaldehyde. A mechanism of Duff reaction was suggested involving the formation of a benzoxazine intermediate. 2005 Pleiades Publishing, Inc.
SEMI-HINDERED PHENOLS. 1. SYNTHESIS OF 3,5-DI-TERT-BUTYLSALICYLIC ALDEHYDE
Dokukina, M. A.,Vol'eva, V. B.,Belostotskaya, I. S.,Komissarova, N. L.,Karmilov, A. Yu.,Ershov, V. V.
, p. 1868 - 1870 (2007/10/02)
Some differences were observed in the solid- and liquid-phase benzylic oxidation of 2-(hydroxy- or dialkylamino)methyl-4,6-di-tert-butylphenols.Oxidation of these semi-hindered phenols with lead tetraacetate gave a new compound: 3,5-di-tert-butyl-ortho-benzoquinone diacylal.Keywords: semi-hindered phenols, synthesis, aldehyde, benzylic alcohol, oxidation, liquid phase, solid phase.