Hydrochloric Acid → 3,5-DI-Tert-butyl-4-hydroxybenzylamine

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Reaction Steps

The covalent bonding of an antioxidant to a polymer to yield (An)nR can also be carried out as follows: first, to 0.1 mole of sodium cyanoborohydride (II), J. Am. Chem. Soc. Vol. 93, pages 2897 to 2904, 1971 and 0.2 mole of ammonium chloride in 50 ml of methanol:50 ml tetrahydrofuran is added sufficient concentrated ammonium hydroxide and concentrated hydrochloric acid alternatively, to give a pH between 5 and 7 as ascertained by touching a drop of the solution to wet universal indicator paper. Next, 0.1 mole of 3,5-di-tert-butyl-4-hydroxybenzaldehyde (I) is added and the reaction stirred for about 4 hours while maintaining the pH of the reaction vessel at about pH 5 to 7. Then, the mixture is treated with 20 ml of 1 molar sodium hydroxide and extracted with 200 ml of a 10:1 volume of ethyl ether: hexane mixture to give 3,5-di-tert-butyl-4-hydroxybenzylamine (III), which is purified by silica gel column chromatography.

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