2-Butylbenzofuran → 2-n-Butyl-3-(3'-methyl-4'-methoxybenzoyl)benzofuran

HRID 1283637Notes

Reaction equation

HRID 1283637 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].[CH2:13]([C:17]1[O:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[CH:21]=1)[CH2:14][CH2:15][CH3:16]>C(=S)=S>[CH2:13]([C:17]1[O:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[C:21]=1[C:5](=[O:6])[C:4]1[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:2]([CH3:1])[CH:3]=1)[CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 779512-ButylbenzofuranHCID 210929304-Methoxy-3-methylbenzoyl chloride

Product 1

HCID 215186372-n-Butyl-3-(3'-methyl-4'-methoxybenzoyl)benzofuran

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 9.4 g. (0.054 mol.) of 2-n-butylbenzofuran in 40 ml. of carbon disulfide was added dropwise over a 20 minute interval 28.2 g. (0.108 mol.) of stannic chloride. After addition, the reaction mixture was warmed to ambient temperature and stirred for two hours. The mixture was then poured onto 100 ml. of ice-water and stirred for one hour. The solvent was removed, the product extracted into chloroform and the extracts were washed with water, dried (Na2SO4) and concentrated in vacuo to give 2-n-butyl-3-(3'-methyl-4'-methoxybenzoyl)benzofuran.

Workup

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

Sources & evidence

ORD record
ord-01bb8d5f5e7d4279bbda5d1748e0f8d5
Source dataset
uspto-grants-1976_08
Patent number
US03975537

Reaction notes

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