Hydrochloric Acid → 2-(4-Methylphenyl)benzofuran-6-carboxylic acid

HRID 566073Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[C:14]#[C:15][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)[C:6]([O:8]CC)=[O:7].[Cl-].[NH+]1C=CC=CC=1.Cl>CN(C=O)C>[CH3:22][C:19]1[CH:20]=[CH:21][C:16]([C:15]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:17][CH:18]=1

Participants

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-23b16f59f8424319bf4c1fa307bc4ecf
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06172061B2

Reaction notes

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