Methyl iodide → Diphenoxymethane

HRID 1243962

Reaction equation

HRID 1243962 reaction equation
[O:1]([C:8]1C=CC(O)=CC=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][C:16](C)([O-:18])[CH3:17].[K+].CI.[CH2:23]1[CH2:27]OC[CH2:24]1>>[O:18]([CH2:8][O:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:16]1[CH:17]=[CH:27][CH:23]=[CH:24][CH:15]=1

Participants

5

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 132544-PhenoxyphenolHCID 23665647Potassium tert-butoxide

Product 1

HCID 78183Diphenoxymethane

Procedure

4-(Phenoxy)phenol (9.31 g, 50 mmol) in THF (100 mL) was treated with potassium t-butoxide (6.17 g, 55 mmol) at room temperature for 10 min. Methyl iodide (7.87 g, 55 mmol) was added by syringe. After stirring for 18 h at room temperature the reaction was quenched with saturated ammonium chloride solution and diluted with ethyl ether. The separated organic layer was washed with saturated ammonium chloride solution, dried with magnesium sulfate, filtered and concentrated to give 9.98 g of the title compound as a pale yellow oil. GS-MS (m/z, EI): 200 [M]+.

Workup

  1. customwas quenched with saturated ammonium chloride solution
  2. additiondiluted with ethyl ether
  3. washThe separated organic layer was washed with saturated ammonium chloride solution
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-191aa6473abc48819fccfa42a9fa38cc
Source dataset
uspto-grants-2006_10
Patent number
US07119201B2

Linked notes

Loading…