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

반응식

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]=1

참가 물질

반응물 4

HCID 313Hydrochloric Acid

HCID 6228Dimethylformamide

HCID 69401Einecs 211-027-4

HCID 18472630Ethyl 3-methoxy-4-(4-methylphenyl)-ethynylbenzoate

생성물 1

HCID 184722332-(4-Methylphenyl)benzofuran-6-carboxylic acid

반응 조건

온도: 200 °C

실험 절차

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).