Hydrochloric Acid → 4-Dibenzofuranol

HRID 2427851Notes

Reaction equation

HRID 2427851 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[C:4](B(O)O)=[CH:3][CH:2]=1.[OH:17]O.Cl>C(OCC)C>[OH:17][C:4]1[C:5]2[O:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[C:9]=2[CH:1]=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 2734328Dibenzofuran-4-boronic acid

Product 1

HCID 30150514-Dibenzofuranol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

4-dibenzofuran boronic acid (4.02 g, 18.9 mmoles) is suspended in diethyl ether (50 mL). The suspension is cooled to 0° C. and hydrogen peroxide (30% in H2O) is added dropwise; the resulting mixture is heated to reflux for 1.5 hours to complete conversion of the starting material. The reaction mixture is then cooled to 0° C. and 1N HCl (4 mL) is added. The organic layer is washed with an aqueous solution containing 10% FeCl2, dried over Na2SO4 and evaporated to dryness to give 3.48 g of the desired compound which is employed in the next step without further purification.

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureto reflux for 1.5 hours
  3. temperatureThe reaction mixture is then cooled to 0° C.
  4. washThe organic layer is washed with an aqueous solution
  5. additioncontaining 10% FeCl2
  6. dry with materialdried over Na2SO4
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-5652f02842984c4aba23ae3c7a98f8a5
Source dataset
uspto-grants-2011_06
Patent number
US07968724B2

Reaction notes

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