Pyridinium chloride → 2-p-Hydroxyphenyl-3-p-methylbenzoylbenzofuran

HRID 1414603Notes

Reaction equation

HRID 1414603 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]=1

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 214879132-p-Methoxyphenyl-3-p-methylbenzoylbenzofuran

Product 1

HCID 214879512-p-Hydroxyphenyl-3-p-methylbenzoylbenzofuran

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

  1. additionThe hot mixture was poured
  2. customthe precipitate formed
  3. extractionwas extracted into ether
  4. dry with materialThe ether solution was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-645498130cf6430187f41de0d2938b75
Source dataset
uspto-grants-1977_01
Patent number
US04001426

Reaction notes

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