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

HRID 1976214Notes

Reaction equation

HRID 1976214 reaction equation
[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

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-644d4b1f7098443785983ae2a6c8536d
Source dataset
uspto-grants-2001_05
Patent number
US06225352B1

Reaction notes

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