Oxalic Acid → 5-Methoxy-6-(1-phenylethyl)-1,3-benzodioxole

HRID 2198437Notes

Reaction equation

HRID 2198437 reaction equation
[CH2:1]1[O:5][C:4]2[CH:6]=[C:7]([OH:10])[CH:8]=[CH:9][C:3]=2[O:2]1.[C:11]1([CH:17](O)[CH3:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:20](O)(=O)C(O)=O>C(O)(=O)C.O>[CH3:18][CH:17]([C:8]1[C:7]([O:10][CH3:20])=[CH:6][C:4]2[O:5][CH2:1][O:2][C:3]=2[CH:9]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH3:18][CH:17]([C:8]1[C:7]([OH:10])=[CH:6][C:4]2[O:5][CH2:1][O:2][C:3]=2[CH:9]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 3

HCID 971Oxalic AcidHCID 74091-PhenylethanolHCID 68289Sesamol

Product 2

HCID 3363375-Methoxy-6-(1-phenylethyl)-1,3-benzodioxoleHCID 13035012(alpha-Methylbenzyl)-3,4-methylenedioxy-6-hydroxybenzene

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

(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.

Workup

  1. distillationDistillation of the oily product
  2. customgave a pale yellow oil, b.p. 204°-205° at 4.0 mm Hg (56 g) which
  3. customcrystallized
  4. customRecrystallization from benzene-skelly solve F

Sources & evidence

ORD record
ord-310097966cae4f64b0bcc50e0923bd49
Source dataset
uspto-grants-1982_11
Patent number
US04357344

Reaction notes

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