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

HRID 66632

Reaction equation

HRID 66632 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-526bccc5f8ae4246aa157ebb8fc29ff9
Source dataset
uspto-grants-1982_08
Patent number
US04342777

Linked notes

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