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

HRID 66630

Reaction equation

HRID 66630 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.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19](O)[CH3:20])=[CH:15][CH:14]=1.[C:22](O)(=O)C(O)=O>C(O)(=O)C.O>[CH3:20][CH:19]([C:8]1[C:7]([O:10][CH3:22])=[CH:6][C:4]2[O:5][CH2:1][O:2][C:3]=2[CH:9]=1)[C:16]1[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 971Oxalic AcidHCID 68289SesamolHCID 1011481-(4-Methoxyphenyl)ethanol

Product 1

HCID 725645-Methoxy-6-[1-(4-methoxyphenyl)ethyl]-1,3-benzodioxole

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

(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).

Workup

  1. extractionextracted with ether
  2. distillationDistillation of the ether
  3. extractionextract
  4. customgave an oil, b.p. 235°-237° at 5 mm Hg (53 g), which
  5. customcrystallized from benzene-skelly solve F
  6. customto yield

Sources & evidence

ORD record
ord-d75f63bf59ec4e51bbd2f9a0df354e58
Source dataset
uspto-grants-1982_08
Patent number
US04342777

Linked notes

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