2-Phenyl-benzofuran → 3-(3-Methyl-4-methoxybenzoyl)-2-phenylbenzofuran

HRID 268379Notes

Reaction equation

HRID 268379 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5](Cl)=[O:6].[C:13]1([C:19]2[O:20][C:21]3[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=3[CH:23]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(=S)=S>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([C:23]1[C:22]2[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=2[O:20][C:19]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:6]

Participants

4

Reactant 2

HCID 35179362-Phenyl-benzofuranHCID 210929304-Methoxy-3-methylbenzoyl chloride

Product 1

HCID 214353193-(3-Methyl-4-methoxybenzoyl)-2-phenylbenzofuran

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a cooled, stirred solution of 10.8 g. (0.058 mol.) of 3-methyl-4-methoxybenzoic acid chloride and 9.6 g. (0.054 mol.) of 2-phenylbenzofuran in 40 ml. of carbon disulfide is added dropwise over a 20 minute interval 28.2 g. (0.108 mol.) of stannic chloride. After addition, the reaction mixture is warmed to ambient temperature and stirred for 2 hours. The mixture is then poured onto 100 ml. of ice-water and stirred for 1 hour. The solvent is removed, and the product extracted into chloroform and the extracts are washed with water, dried (Na2SO4) and concentrated under reduced pressure to give 3-(3-methyl-4-methoxybenzoyl)-2-phenylbenzofuran.

Workup

  1. additionAfter addition
  2. stirringstirred for 2 hours
  3. additionThe mixture is then poured onto 100 ml
  4. customThe solvent is removed
  5. extractionthe product extracted into chloroform
  6. washthe extracts are washed with water
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-462a09f066324439b8f5a7ca85494815
Source dataset
uspto-grants-1976_03
Patent number
US03947470

Reaction notes

Loading…