Hydrochloric Acid → 6-Methyl-1-benzofuran-2-carboxylic acid

HRID 1773219Notes

Reaction equation

HRID 1773219 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:4]=1[O:5][CH2:6][C:7]#N)=O.[OH-:14].[K+].Cl.[OH2:17]>CCO>[CH3:13][C:10]1[CH:11]=[CH:12][C:3]2[CH:1]=[C:6]([C:7]([OH:17])=[O:14])[O:5][C:4]=2[CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 118452708HCID 118452708, compound

Product 1

HCID 202609456-Methyl-1-benzofuran-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(2-formyl-5-methylphenoxy)acetonitrile (11.12 g, 63.5 mmol) in 244 mL of EtOH was added KOH (14.85 g, 265 mmol), and the mixture was refluxed overnight. The reaction mixture was cooled to room temperature and the solvent was evaporated until a thick slurry was obtained, which was diluted with 204 mL H2O. To the resulting solution was added concentrated HCl, a white precipitate formed, and the mixture was filtered, the solid was washed with H2O and dried under the vacuum oven at 50° C. to yield 6-methylbenzofuran-2-carboxylic acid (11.2 g). LCMS retention time=1.00 minutes (LC method 3); MS (m−1)=175.0. 1H NMR (400 MHz, DMSO-d6) δ 2.45 (s, 3H), 7.13-7.18 (m, 1H), 7.47 (s, 2H), 7.62 (d, J=8.0 Hz, 1H).

Workup

  1. temperaturethe mixture was refluxed overnight
  2. customthe solvent was evaporated until a thick slurry
  3. customwas obtained
  4. customa white precipitate formed
  5. filtrationthe mixture was filtered
  6. washthe solid was washed with H2O
  7. customdried under the vacuum oven at 50° C.

Sources & evidence

ORD record
ord-39e739e518464020be143715afe9f931
Source dataset
uspto-grants-2016_02
Patent number
US09255093B2

Reaction notes

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