Hydrochloric Acid → 7-Methoxybenzofuran

HRID 1978774Notes

Reaction equation

HRID 1978774 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[O:10][C:9](C(O)=O)=[CH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.Cl>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[CH3:1][O:2][C:3]1[C:11]2[O:10][CH:9]=[CH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 6060377-Methoxy-1-benzofuran-2-carboxylic acid

Product 1

HCID 5904627-MethoxybenzofuranYield 96.2%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7047QuinolineSolvent

Procedure

A suspension of 7-methoxybenzofuran-2-carboxylicacid (11.04 g) and copper powder (1.83 g) in quinoline (200 ml) was refluxed under nitrogen atmosphere for 2 hours and cooled, and to the suspension was added 2N hydrochloric acid. The mixture was extracted with ethyl acetate, and the organic layer was washed with 2N hydrochloric acid (8 times), 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 7-methoxybenzofuran (8.19 g).

Workup

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

Sources & evidence

ORD record
ord-bcd867b7ae5f4ddca44d9a4dec83498c
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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