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

HRID 1979846

Reaction equation

HRID 1979846 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-86d914704acb4748b5efeaa4ee68b4a1
Source dataset
uspto-grants-1984_11
Patent number
US04482728

Linked notes

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