تفاعل #94910

معادلة التفاعل

sesamol

1-phenylethyl alcohol

oxalic acid

→

(α-Methylbenzyl)-3,4-methylenedioxy-6-methoxybenzene

(α-methylbenzyl)-3,4-methylenedioxy-6-hydroxybenzene

المذيبات

acetic acid

water

water

ظروف التفاعل

المعالجة

1. 1
   workup.DISTILLATIONDistillation of the oily product
2. 2
   أخرىgave a pale yellow oil, b.p. 204°-205° at 4.0 mm Hg (56 g) which
3. 3
   أخرىcrystallized
4. 4
   أخرىRecrystallization from benzene-skelly solve F

الإجراء التجريبي

(α-Methylbenzyl)-3,4-methylenedioxy-6-methoxybenzene was prepared as follows: A solution of sesamol (41.4 g), 1-phenylethyl alcohol (36.6 g) and oxalic acid (2 g) in acetic acid (100 ml) and water (10 ml) was refluxed for 24 hours and diluted with water. Distillation of the oily product gave a pale yellow oil, b.p. 204°-205° at 4.0 mm Hg (56 g) which crystallized. Recrystallization from benzene-skelly solve F gave (α-methylbenzyl)-3,4-methylenedioxy-6-hydroxybenzene as colorless needles, m.p. 101°-102° (Found: C, 74.2, H, 5.75. Calc. for C15H14O3 : C, 74.4; H, 5.83%); pmr spectrum: δ1.57, 3H, D (J=7 Hz); δ4.29, 1H, Q (J=7 Hz); δ4.50, 1H, S; δ5.86, 2H, S; δ6.35, 1H, S; δ6.72, 1H, S; δ7.25, 5H, S.

المصدر