Oxalic Acid → 2,4-Bis(1,1-dimethylethyl)-6-((4-methoxyphenyl)methyl)phenol

Beteiligte Stoffe

Reaktionsschritte

4,6-Di-t-butyl-2-(4-methoxybenzyl) phenol was prepared as follows: A solution of 2,4-di-t-butylphenol (57.5 g), 4-methoxybenzyl alcohol (34.5 g) and oxalic acid (2 g) in acetic acid (80 ml) and water (2 ml) was refluxed for 7 hours, diluted with water, and extracted with chloroform. Distillation of the chloroform extract gave an oil (b.p. 200°-210° C. at 2 mm Hg) which crystallized (58 g; 71.4%). The product was recrystallized from methanol to give glistening colorless needles, m.p. 84°-85°; (Found: C, 81.0; H, 9.21. Calc. for C22H30O2 : C, 80.9; H, 9.26%). The pmr spectrum exhibited the following: δ1.30, 9H, S; δ1.38, 9H, S; δ3.79, 3H, S; δ3.83, 2H, S; δ4.62, 1H, S; δ6.84, 2H, D (J=8 Hz); δ7.02, 1H, D (J=2 Hz); δ7.14, 2H, D (J=8 Hz); δ7.23, 1H, D (J=Hz).

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