Hydrochloric Acid → 6-Hydroxybenzofuran

HRID 1978770Notes

Reaction equation

HRID 1978770 reaction equation
C[O:2][C:3]1[CH:11]=[CH:10][C:6]2[CH:7]=[CH:8][O:9][C:5]=2[CH:4]=1.[I-].[Li+].Cl>N1C(C)=CC(C)=CC=1C>[OH:2][C:3]1[CH:11]=[CH:10][C:6]2[CH:7]=[CH:8][O:9][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 66321Lithium iodideHCID 53144106-Methoxybenzofuran

Product 1

HCID 1288446-HydroxybenzofuranYield 19%

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Procedure

To a solution of 6-methoxybenzofuran (16.9 g) in collidine (200 ml) was added lithium iodide (30.5 g), and the mixture was refluxed under argon atmosphere for 1 day and cooled. To the mixture was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with 2N hydrochloric acid (5 times) and then washed with water and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography to give dark brown oil of 6-hydroxybenzofuran (2.9 g).

Workup

  1. temperaturethe mixture was refluxed under argon atmosphere for 1 day
  2. temperaturecooled
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with 2N hydrochloric acid (5 times)
  5. washwashed with water and saturated brine
  6. dry with materialdried with magnesium sulfate
  7. customUnder reduced pressure, the solvent was evaporated
  8. customthe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-6b3bf1bfc04347e3a76633c747fd1604
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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