Potassium Carbonate → 1-[3,5-Dimethoxy-benzyloxy]-2-[toluene-4-sulfonyloxy]benzene

HRID 1976208Notes

Reaction equation

HRID 1976208 reaction equation
[C:1]1([CH3:18])[CH:6]=[CH:5][C:4]([S:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])(=[O:9])=[O:8])=[CH:3][CH:2]=1.BrC[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=1[O:29][CH3:30].[C:31](=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CC(C)=O>[CH3:28][O:27][C:24]1[CH:25]=[C:26]([CH:21]=[C:22]([O:29][CH3:30])[CH:23]=1)[CH2:31][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[O:10][S:7]([C:4]1[CH:3]=[CH:2][C:1]([CH3:18])=[CH:6][CH:5]=1)(=[O:8])=[O:9]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 17221462-Hydroxyphenyl 4-methylbenzenesulfonateHCID 151519071-(Bromomethyl)-2,4-dimethoxybenzene

Product 1

HCID 220006591-[3,5-Dimethoxy-benzyloxy]-2-[toluene-4-sulfonyloxy]benzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Toluene-4-sulfonic acid, 2-hydroxyphenyl ester (0.64 g, 2.42 mmol), 4-bromomethyl-1,3-dimethoxy-benzene (0.56 g, 2.42 mmol), potassium carbonate (0.36 g, 2.62 mmol) and 18-crown-6-ether (0.06 g, 0.24 mmol) were stirred together at room temperature in acetone (20 cm3, 99%) under nitrogen for 28 hours. The solution was evaporated under reduced pressure, and the residue was taken up in dichloromethane (20 cm3) and water (20 cm3). The aqueous layer was extracted with dichloromethane (2×20 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 ether, (0.84 g, 83%) as a clear oil.

Workup

  1. customThe solution was evaporated under reduced pressure
  2. extractionThe aqueous layer was extracted with dichloromethane (2×20 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 ether, (0.84 g, 83%) as a clear oil

Sources & evidence

ORD record
ord-25215e3234eb419f9704a9e5c703f5c4
Source dataset
uspto-grants-2001_05
Patent number
US06225352B1

Reaction notes

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