Pyrogallol → 4-(3,5-Dimethoxy-benzyloxy)-2-ethoxy-benzo[1,3]dioxole

HRID 1976214Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1976214
[CH2:1]([O:3][CH:4]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[C:12]([OH:13])[C:6]=2[O:5]1)[CH3:2].BrC[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=1[O:24][CH3:25].[C:26](=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.C1(C=CC=C(O)C=1O)O>CC(C)=O>[CH3:23][O:22][C:19]1[CH:20]=[C:21]([CH:16]=[C:17]([O:24][CH3:25])[CH:18]=1)[CH2:26][O:13][C:12]1[C:6]2[O:5][CH:4]([O:3][CH2:1][CH3:2])[O:8][C:7]=2[CH:9]=[CH:10][CH:11]=1

Komponenten

7

Edukt 5

HCID 1057PyrogallolHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 134470632-Ethoxy-benzo[1,3]dioxol-4-olHCID 151519071-(Bromomethyl)-2,4-dimethoxybenzene

Produkt 1

HCID 220006654-(3,5-Dimethoxy-benzyloxy)-2-ethoxy-benzo[1,3]dioxole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

2-Ethoxy-benzo[1,3]dioxol-4-ol (1.11 g, 6.08 mmol), 4-bromomethyl-1,3-dimethoxybenzene (1.17 g, 5.08 mmol), potassium carbonate (0.77 g, 5.59 mmol) and 18-crown-6-ether (0.13 g, 0.51 mmol) were stirred together at room temperature in acetone (40 cm3, 99%) under nitrogen for 18 hours. The solution was evaporated under reduced pressure, and the residue was taken up in dichloromethane (30 cm3) and water (30 cm3). The aqueous layer was extracted with dichloromethane (3×30 cm3), and the combined extracts were washed with water (2×50 cm3), dried (MgSO4), and evaporated under reduced pressure. The residue was chromatographed (SiO2, dichloromethane) to give the di protected pyrogallol, (1.56 g, 92%) as a clear oil.

Aufarbeitung

  1. customThe solution was evaporated under reduced pressure
  2. extractionThe aqueous layer was extracted with dichloromethane (3×30 cm3)
  3. washthe combined extracts were washed with water (2×50 cm3)
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customThe residue was chromatographed (SiO2, dichloromethane)
  7. customto give the di

Quellen und Nachweise

ORD-Eintrag
ord-644d4b1f7098443785983ae2a6c8536d
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06225352B1

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