Reaction #2195473

ord-043dc0a2b807409b8a6633c7a76e8f91

Reaction equation

Oc1ccccc1
phenol
[H-].[Na+]
sodium hydride
Cl
HCl
→
c1ccc2c(c1)oc1ccccc12
Dibenzofuran

Reactants

Oc1ccccc1
phenol
[H-].[Na+]
sodium hydride
Cl
HCl

Reagents

None

Solvents

CS(C)=O
DMSO

Conditions

Temperature
120°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    ExtractionThe aqueous phase is extracted with MTB ether
  2. 2
    DryingThe organic phase is dried over sodium sulfate
  3. 3
    Otherevaporated
  4. 4
    Otherchromatographed on silica gel

Procedure

The phenol 10 is dissolved in DMSO under nitrogen, a 60% sodium hydride/mineral oil suspension is added, and the mixture is warmed to 120° C. After 5 hours at this temperature, the cooled batch is added to dil. HCl solution. The aqueous phase is extracted with MTB ether. The organic phase is dried over sodium sulfate, evaporated and chromatographed on silica gel.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07514127B2uspto-grants-2009_04