Resorcinol → 3-[3,5-Dimethoxy-benzyloxy]-phenol

HRID 1976211Notes

Reaction equation

HRID 1976211 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].BrC[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=1[O:19][CH3:20].[C:21](=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CC(C)=O>[CH3:18][O:17][C:14]1[CH:15]=[C:16]([CH:11]=[C:12]([O:19][CH3:20])[CH:13]=1)[CH2:21][O:2][C:1]1[CH:3]=[C:4]([OH:5])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 5054ResorcinolHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 151519071-(Bromomethyl)-2,4-dimethoxybenzene

Product 1

HCID 220006553-[3,5-Dimethoxy-benzyloxy]-phenolYield 27.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Resorcinol (0.21 g, 1.87 mmol), 4-bromomethyl-1,3-dimethoxybenzene (0.39 g, 1.70 mmol), potassium carbonate (0.26 g, 1.87 mmol) and 18-crown-6-ether (0.09 g, 0.34 mmol) were stirred together in acetone (15 cm3, 99%) under nitrogen at room temperature for 20 hours. The solution was evaporated under reduced pressure, and the residue was taken up in dichloromethane (10 cm3) and water (10 cm3). The aqueous layer was extracted with dichloromethane (2×10 cm3), and the combined extracts were washed with water (2×20 cm3), dried (MgSO4), and evaporated under reduced pressure. The residue was chromatographed (SiO2, dichloromethane) to give the phenol, (0.12 g, 27%), as an oil.

Workup

  1. customThe solution was evaporated under reduced pressure
  2. extractionThe aqueous layer was extracted with dichloromethane (2×10 cm3)
  3. washthe combined extracts were washed with water (2×20 cm3)
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customThe residue was chromatographed (SiO2, dichloromethane)

Sources & evidence

ORD record
ord-bfb336cbad644629a1cc2e99b968ade7
Source dataset
uspto-grants-2001_05
Patent number
US06225352B1

Reaction notes

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