Hydrochloric Acid → 2-(4-Methylphenyl)benzofuran-5-carboxylic acid

HRID 2228258Notes

Reaction equation

HRID 2228258 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][C:11]=3[CH:12]=2)=[CH:4][CH:3]=1.CC1CCCCC=1.Cl([O-])=[O:27].[Na+].P([O-])(O)(O)=O.[Na+].Cl>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([C:17]([OH:27])=[O:18])=[CH:13][C:11]=3[CH:12]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 115741-MethylcyclohexeneHCID 184722462-(4-Methylphenyl)benzofuran-5-carbaldehydeHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 184722092-(4-Methylphenyl)benzofuran-5-carboxylic acidYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-methylphenyl)benzofuran-5-carbaldehyde (500 mg) and 1-methylcyclohexene (1.2 ml) in DMF (15 ml) was added a solution (9 ml) of sodium chlorite (80%, 1.5 g) and sodium dihydrogenphosphate (1.5 g) at room temperature, and the mixture was stirred for 3 hours. To the mixture was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with sodium thiosulfate and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the mixture was concentrated, and the precipitated crystals were collected by filtration, which were washed with diethylether to give colorless crystals of 2-(4-methylphenyl)benzofuran-5-carboxylic acid (395 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with sodium thiosulfate and saturated brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationUnder reduced pressure, the mixture was concentrated
  5. filtrationthe precipitated crystals were collected by filtration, which
  6. washwere washed with diethylether

Sources & evidence

ORD record
ord-26d1433307864106985c7e2382648307
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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