Dichloromethane → 2-p-Methoxyphenyl-3-p-methylbenzoylbenzofuran

HRID 1414602Notes

Reaction equation

HRID 1414602 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[CH:13]=2)=[CH:5][CH:4]=1.[C:18]1([CH3:27])[CH:23]=[CH:22][C:21]([C:24](Cl)=[O:25])=[CH:20][CH:19]=1.C(Cl)Cl>O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[C:13]=2[C:24](=[O:25])[C:21]2[CH:22]=[CH:23][C:18]([CH3:27])=[CH:19][CH:20]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 134054-Methylbenzoyl ChlorideHCID 107278342-(4-Methoxyphenyl)benzofuran

Product 1

HCID 214879132-p-Methoxyphenyl-3-p-methylbenzoylbenzofuran

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a cooled (0°) mixture of 4.07 g. (0.018 mol.) of 2-p-methoxyphenylbenzofuran and 4.17 g. (0.027 mol.) of p-toluic acid chloride in 100 ml. of methylene chloride was added dropwise 11.25 g. (0.043 mol.) of stannic chloride. The reaction mixture was stirred for 1.5 hours at 0°, then for 0.5 hour at 25 °. The mixture was poured into water and stirred vigorously, the layers were separated and the organic phase was washed with saturated aqueous sodium bicarbonate, dried (MgSO4) and concentrated to give 2-p-methoxyphenyl-3-p-methylbenzoylbenzofuran.

Workup

  1. temperatureTo a cooled
  2. addition(0°) mixture of 4.07 g
  3. waitfor 0.5 hour at 25 °
  4. stirringstirred vigorously
  5. customthe layers were separated
  6. washthe organic phase was washed with saturated aqueous sodium bicarbonate
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-87f9558797f74ac38d5e2875d0f0ed9c
Source dataset
uspto-grants-1977_01
Patent number
US04001426

Reaction notes

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