Water → 2-(4-Methylphenyl)benzofuran-5-carbaldehyde

HRID 1388000Notes

Reaction equation

HRID 1388000 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][C:5]([C:6](=NOC2C=CC(C=O)=CC=2)[CH3:7])=[CH:4][CH:3]=1.[OH2:20].Cl.[C:22]([OH:25])(=O)[CH3:23]>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]2[O:20][C:2]3[CH:19]=[CH:18][C:23]([CH:22]=[O:25])=[CH:4][C:3]=3[CH:7]=2)=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 962WaterHCID 22641269Acetate-hydrochloric acidHCID 867561784-(4'-Methyl-alpha-methylbenzylideneaminoxy)benzaldehyde

Product 1

HCID 184722462-(4-Methylphenyl)benzofuran-5-carbaldehyde

Procedure

A solution of 4-(4′-methyl-α-methylbenzylidene-aminoxy)benzaldehyde (5.0 g) in 1N hydrochloric acid/acetic acid (80 ml) was stirred at 100-110° C. for 24 hours and then cooled to room temperature. To the mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the mixture was concentrated, and the residue was purified with column chromatography (ethyl acetate/hexane=1:9) to give colorless crystals of 2-(4-methylphenyl)benzofuran-5-aldehyde (1.50 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationUnder reduced pressure, the mixture was concentrated
  5. customthe residue was purified with column chromatography (ethyl acetate/hexane=1:9)

Sources & evidence

ORD record
ord-8803e23970604852a31697ee1a22ae4c
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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