Potassium Carbonate → HCID 22000664, compound

HRID 1976212Notes

Reaction equation

HRID 1976212 reaction equation
[CH3:1][C:2]1[C:8]([OH:9])=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4].BrC[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=1[O:20][CH3:21].[C:22](=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CC(C)=O>[CH3:19][O:18][C:15]1[CH:16]=[C:17]([CH:12]=[C:13]([O:20][CH3:21])[CH:14]=1)[CH2:22][O:4][C:3]1[C:2]([CH3:1])=[C:8]([OH:9])[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 118432-MethylresorcinolHCID 2855718-Crown-6HCID 151519071-(Bromomethyl)-2,4-dimethoxybenzene

Product 1

HCID 22000664HCID 22000664, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Methyl resorcinol (0.07 g, 0.59 mmol), 4-bromomethyl-1,3-dimethoxybenzene (0.13 g, 0.55 mmol), potassium carbonate (0.09 g, 0.68 mmol) and 18-crown-6-ether (0.03 g, 0.11 mmol) were combined in acetone (15 cm3, 99%) and heated to reflux under nitrogen for 22 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, (0.02 g, 15%), as a white solid, mp 63-69° C.

Workup

  1. temperatureheated
  2. temperatureto reflux under nitrogen for 22 hours
  3. customThe solution was evaporated under reduced pressure
  4. extractionThe aqueous layer was extracted with dichloromethane (2×10 cm3)
  5. washthe combined extracts were washed with water (2×20 cm3)
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure
  8. customThe residue was chromatographed (SiO2, dichloromethane)

Sources & evidence

ORD record
ord-fc741e6133ba47338615e1e3525404e5
Source dataset
uspto-grants-2001_05
Patent number
US06225352B1

Reaction notes

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