Hydrochloric Acid → 6-Methoxybenzofuran

HRID 1978769Notes

Reaction equation

HRID 1978769 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[CH:7]=[C:8](C(O)=O)[O:9][C:5]=2[CH:4]=1.Cl>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[CH:7]=[CH:8][O:9][C:5]=2[CH:4]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 9188636-Methoxy-1-benzofuran-2-carboxylic acid

Product 1

HCID 53144106-MethoxybenzofuranYield 99.9%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7047QuinolineSolvent

Procedure

A suspension of 6-methoxybenzofuran-2-carboxylic acid (22.2 g) and copper powder (3.7 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 (6 times) and then washed with water and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated to give dark brown oil of 6-methoxybenzofuran (17.1 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 (6 times)
  5. washwashed with water and saturated brine
  6. dry with materialdried with magnesium sulfate
  7. customUnder reduced pressure, the solvent was evaporated

Sources & evidence

ORD record
ord-ad9c600e28ec45e0ac002ee66d588a62
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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