Pyridinium chloride → 2-p-Hydroxyphenyl-3-p-methylbenzoylbenzofuran
Reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:26]=[CH:25][CH:24]=[CH:23][C:12]=3[C:13]=2[C:14](=[O:22])[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[CH:5][CH:4]=1.Cl.N1C=CC=CC=1>>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:10][C:11]3[CH:26]=[CH:25][CH:24]=[CH:23][C:12]=3[C:13]=2[C:14](=[O:22])[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[CH:7][CH:8]=1Participants
3
Procedure
2-p-Methoxyphenyl-3-p-methylbenzoylbenzofuran (4.9 g., 0.014 mol.) was combined with 50 g. of freshly distilled pyridine hydrochloride and the mixture was heated at 180°-190° for 4.5 hours. The hot mixture was poured with stirring onto an ice-5% aqueous hydrochloric acid mixture and the precipitate formed was extracted into ether. The ether solution was dried (MgSO4) and concentrated under reduced pressure to give 2-p-hydroxyphenyl-3-p-methylbenzoylbenzofuran.
Workup
- additionThe hot mixture was poured
- customthe precipitate formed
- extractionwas extracted into ether