[C:1]([BH3-])#[N:2].[Na+].[Cl-].[NH4+].[OH-].[NH4+].Cl.[C:10]([C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:21]=1[OH:22])C=O)([CH3:13])([CH3:12])[CH3:11].[OH-].[Na+]>CO.O1CCCC1>[C:23]([C:20]1[CH:19]=[C:16]([CH:15]=[C:14]([C:10]([CH3:13])([CH3:12])[CH3:11])[C:21]=1[OH:22])[CH2:1][NH2:2])([CH3:26])([CH3:25])[CH3:24]The covalent bonding of an antioxidant to a polymer to yield (An)n ~R 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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