Potassium Iodide → Dibenzyl ether

HRID 2199870Notes

Reaction equation

HRID 2199870 reaction equation
C[C:2]1[CH:3]=[C:4]([CH:9]=[C:10](C)[C:11]=1O)[C:5]([O:7][CH3:8])=O.Br[CH2:15][CH2:16][CH2:17][CH3:18].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[C:27](OCC)(=O)[CH3:28]>CN(C=O)C>[CH2:8]([O:7][CH2:5][C:4]1[CH:3]=[CH:2][CH:11]=[CH:10][CH:9]=1)[C:15]1[CH:28]=[CH:27][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 8002Butyl bromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 12389264Methyl 4-hydroxy-3,5-dimethylbenzoate

Product 1

HCID 7657Dibenzyl ether

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 3,5-dimethyl-4-hydroxybenzoate represented by Formula 146 (1.72 g, 9.52 mmol), 1-bromobutane (1.13 mL, 10.47 mmol), potassium carbonate (K2CO3, 1.45 g, 10.47 mmol) and potassium iodide (KI, 158 mg, 0.95 mmol) in DMF (20 mL) was agitated at 80° C. for 24 hours. After decreasing a temperature of the reaction mixture to room temperature, solids were removed through filtration (and washed with acetone) to obtain a filtrate. After adding ethyl acetate to the filtrate, the solution was consecutively washed with water and a 5N HCl solution. After separating an organic layer and drying the same with magnesium sulfate (MgSO4), the solvent was removed under reduced pressure to prepare a concentrate mixture. This mixture was subjected to separation and purification through column chromatography (ethyl acetate/hexane, 1:5, v/v) using silica gel (SiO2), resulting in a benzylether compound represented by Formula 147 as a desired product (2.1 g, 93%). Analysis data of the product is provided as follows:

Workup

  1. customto room temperature
  2. customsolids were removed through filtration (and washed with acetone)
  3. customto obtain a filtrate
  4. washthe solution was consecutively washed with water
  5. customAfter separating an organic layer
  6. dry with materialdrying the same with magnesium sulfate (MgSO4)
  7. customthe solvent was removed under reduced pressure
  8. customto prepare a concentrate mixture
  9. customThis mixture was subjected to separation and purification through column chromatography (ethyl acetate/hexane, 1:5

Sources & evidence

ORD record
ord-32f9e657e8144a358d54c847ed274621
Source dataset
uspto-grants-2016_06
Patent number
US09359346B2

Reaction notes

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