Hydrochloric Acid → Dibenzofuran

HRID 2108291Notes

Reaction equation

HRID 2108291 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl>CS(C)=O>[CH:5]1[C:6]2[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=3[O:7][C:1]=2[CH:2]=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 996PhenolHCID 24758Sodium hydride

Product 1

HCID 568Dibenzofuran

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

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.

Workup

  1. extractionThe aqueous phase is extracted with MTB ether
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customevaporated
  4. customchromatographed on silica gel

Sources & evidence

ORD record
ord-043dc0a2b807409b8a6633c7a76e8f91
Source dataset
uspto-grants-2009_04
Patent number
US07514127B2

Reaction notes

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