Oxalic Acid → 5-Methoxy-6-[1-(4-methoxyphenyl)ethyl]-1,3-benzodioxole

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(α-Methyl-4-methoxybenzyl)-3,4-methylenedioxy-6-methoxybenzene was prepared according to the following procedure: A solution of sesamol (27.6 g, 0.2 mole), 1-(4-methoxyphenyl)ethanol (30.4 g, 0.2 mole), and oxalic acid (2 g) in glacial acetic acid (60 ml) and water (10 ml) was refluxed for 7 hours, diluted with water, and extracted with ether. Distillation of the ether extract gave an oil, b.p. 235°-237° at 5 mm Hg (53 g), which crystallized from benzene-skelly solve F to yield glistening, colorless needles, m.p. 93°-94° (Found: C, 70.5; H, 5.86. Calc. for C16H16O4 : C, 70.6; H, 5.92%); pmr spectrum: δ1.53, 3H, D (J=7 Hz); δ3.77, 3H, S; δ4.21, 1H, Q (J=7 Hz); δ4.58, 1H (OH), S; δ5.86, 2H, S; δ6.35, 1H, S; δ6.70, 1H, S; δ6.81, 2H, D (J=9 Hz); δ7.17, 2H, D (J=9 Hz).

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