Boron trifluoride etherate → 1,1'-[Oxybis(methylene)]bis(4-methoxybenzene)

HRID 1648333Notes

Reaction equation

HRID 1648333 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7]N=C([O-])C(Cl)(Cl)Cl)=[CH:5][CH:4]=1.B(F)(F)F.C[CH2:22][O:23][CH2:24][CH3:25].[C:26]([O-:29])(O)=O.[Na+]>C(Cl)Cl>[CH3:22][O:23][C:24]1[CH:25]=[CH:5][C:4]([CH2:26][O:29][CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:16][CH:15]=2)=[CH:3][CH:16]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 86748078HCID 86748078, compound

Product 1

HCID 2211761,1'-[Oxybis(methylene)]bis(4-methoxybenzene)Yield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred 0° C. solution of the alcohol (755 mg, 1.22 mmol) and p-methoxybenzyltrichloroacetimidate (3.446 g, 12.2 mmol) in CH2Cl2 (120 mL) at 0° C. was added a 0.1 M solution of BF3.OEt2 in CH2Cl2 (50 μL). The resulting orange solution was stirred for 10 min, at which time TLC showed no remaining starting material. Saturated aqueous NaHCO3 (40 mL) was added, and after vigorous mixing the separated organic phase was dried over Na2SO4, filtered, and concentrated. The residue was chromatographed on silica gel (hexanes/ethyl acetate; 5:1) to give the p-methoxybenzyl ether (866 mg, 1.17 mmol, 96% yield) as a clear oil.

Workup

  1. additionafter vigorous mixing the separated organic phase
  2. dry with materialwas dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel (hexanes/ethyl acetate; 5:1)

Sources & evidence

ORD record
ord-ab5dd25eb8e74369995a77666401363e
Source dataset
uspto-grants-1995_07
Patent number
US05436238

Reaction notes

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