Hydrochloric Acid → Benzofuran-5-ol

HRID 1978766Notes

Reaction equation

HRID 1978766 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][CH:9]=[CH:8][C:7]=2[CH:11]=1.[I-].[Li+].Cl>N1C(C)=CC(C)=CC=1C>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][CH:9]=[CH:8][C:7]=2[CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 259435-MethoxybenzofuranHCID 66321Lithium iodide

Product 1

HCID 11651159Benzofuran-5-olYield 49.1%

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Procedure

To a solution of 5-methoxybenzofuran (3.6 g) in collidine (20 ml) was added lithium iodide (6.5 g), and the mixture was refluxed, under argon atmosphere, overnight, cooled, made acidic (pH=4) with hydrochloric acid and extracted with ethyl acetate (three times). The organic layer was washed with 1N hydrochloric acid (twice) 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 yellow oil of 5-hydroxybenzofuran (1.6 g).

Workup

  1. temperaturethe mixture was refluxed, under argon atmosphere, overnight
  2. temperaturecooled
  3. extractionextracted with ethyl acetate (three times)
  4. washThe organic layer was washed with 1N hydrochloric acid (twice) and
  5. washthen washed 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-753eeade6f5741bd8c6dc1884759e93c
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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