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

反応式

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

参加物

反応物 4

HCID 313Hydrochloric Acid

HCID 6228Dimethylformamide

HCID 69401Einecs 211-027-4

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

生成物 1

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

反応条件

温度: 200 °C

実験手順

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).