Hydrochloric Acid → 2-(4-Methylphenyl)benzofuran-6-carboxylic acid
Reaction equation
C[O:2][C:3]1[C:4](C#C)=[C:5]([CH:11]=[CH:12][C:13]=1[C:14]1[CH:19]=[CH:18][C:17](C)=[CH:16][CH:15]=1)[C:6]([O:8]CC)=[O:7].[Cl-].[NH+]1C=CC=[CH:26][CH:25]=1.Cl.[CH3:31]N(C=O)C>>[CH3:31][C:15]1[CH:16]=[CH:17][C:18]([C:19]2[O:2][C:3]3[CH:4]=[C:5]([C:6]([OH:8])=[O:7])[CH:11]=[CH:12][C:13]=3[CH:14]=2)=[CH:26][CH:25]=1Participants
5
Conditions
- Temperature
- 200 °C
Procedure
A mixture of ethyl 3-methoxy-4-(4-methylphenyl)-ethynylbenzoate (1.5 g) and pyridinium chloride (9.0 g) was stirred at 200° C. for 2 hours, and then cooled to 100° C. To the mixture was added DMF (20 ml), and the mixture was cooled to room temperature. To the mixture was added 1N hydrochloric acid, 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 precipitated crystals were collected by filtration, which were washed with diethylether and hexane to give pale yellow crystals of 2-(4-methylphenyl)benzofuran-6-carboxylic acid (0.84 g).
Workup
- temperaturecooled to 100° C
- temperaturethe mixture was cooled to room temperature
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried with magnesium sulfate
- concentrationUnder reduced pressure, the mixture was concentrated
- filtrationthe precipitated crystals were collected by filtration, which
- washwere washed with diethylether and hexane
Sources & evidence
- ORD record
- ord-122b5cd5b53e43c080eb061ef9c53d82
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06268354B1
Reaction notes
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