Methyl iodide → 4-Methoxydibenzofuran

HRID 2427852Notes

Reaction equation

HRID 2427852 reaction equation
[OH:1][C:2]1[C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:15]([O-])([O-])=O.[K+].[K+].IC>CC(C)=O>[CH3:15][O:1][C:2]1[C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 30150514-Dibenzofuranol

Product 1

HCID 119941974-MethoxydibenzofuranYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

4-hydroxy-dibenzofuran (5.19 g, 28.2 mmoles) is dissolved in acetone (175 mL) under nitrogen atmosphere. Solid K2CO3 (5.85 g, 42.3 mmoles) and iodomethane (7.9 mL, 126.9 mmoles) are added and the resulting mixture is vigorously stirred to reflux (40° C.) to complete conversion of the starting material (7h). The reaction mixture is evaporated to dryness, the crude is then dissolved in water and extracted with DCM; the combined organic layers are washed again with water and brine, dried over sodium sulphate and evaporated to dryness to give the desired product as a white solid (5.48 g) which is employed in the next step without further purification.

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. dissolutionthe crude is then dissolved in water
  3. extractionextracted with DCM
  4. washthe combined organic layers are washed again with water and brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-b4f0ad38c9cd41d894d74ba1df3469f6
Source dataset
uspto-grants-2011_06
Patent number
US07968724B2

Reaction notes

Loading…