1,2-Dichlorobenzene → 2-(p-Methoxybenzoyl)-3-methyl-4-hydroxy-5-allylbenzofuran

HRID 1534241Notes

Reaction equation

HRID 1534241 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([C:7]([C:9]2[O:10][C:11]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19]CC=C)[C:12]=3[C:13]=2[CH3:14])=[O:8])=[CH:5][CH:4]=1.Cl[C:26]1[CH:31]=CC=C[C:27]=1Cl>>[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([C:7]([C:9]2[O:10][C:11]3[CH:18]=[CH:17][C:16]([CH2:31][CH:26]=[CH2:27])=[C:15]([OH:19])[C:12]=3[C:13]=2[CH3:14])=[O:8])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 72391,2-DichlorobenzeneHCID 150296682-(p-Methoxybenzoyl)-3-methyl-4-allyloxybenzofuran

Product 1

HCID 145797922-(p-Methoxybenzoyl)-3-methyl-4-hydroxy-5-allylbenzofuranYield 93%

Procedure

A solution of 2-(p-methoxybenzoyl)-3-methyl-4-allyloxybenzofuran (0.7 gm; 2.2 mmoles) in orthodichlorobenzene (3 mL) was refluxed under nitrogen for a period of 4 hours. The mixture was cooled to rom temperature and purified by chromatography on silica gel using 15% ethylacetate in hexane as eluent to yield 650 mg (93%) of 2-(p-methoxybenzoyl)-3-methyl-4-hydroxy-5-allylbenzofuran, mp. 48°-50° C.

Workup

  1. temperatureThe mixture was cooled
  2. custompurified by chromatography on silica gel using 15% ethylacetate in hexane as eluent

Sources & evidence

ORD record
ord-0b0e9bf7d21d48f389a4d7ca101fb811
Source dataset
uspto-grants-1992_02
Patent number
US05087638

Reaction notes

Loading…