Trifluoroacetic acid → 2-n-Butyl-3-(3'-methoxy-4'-hydroxybenzoyl)-benzofuran

HRID 1283659Notes

Reaction equation

HRID 1283659 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[CH:9]=1)[CH2:2][CH2:3][CH3:4].C([O:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#N)=[CH:20][C:19]=1[O:26][CH3:27])(=O)C.FC(F)(F)C(O)=[O:31]>>[CH2:1]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[C:9]=1[C:22](=[O:31])[C:21]1[CH:24]=[CH:25][C:18]([OH:17])=[C:19]([O:26][CH3:27])[CH:20]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 779512-ButylbenzofuranHCID 7937734-Cyano-2-methoxyphenyl acetate

Product 1

HCID 215185992-n-Butyl-3-(3'-methoxy-4'-hydroxybenzoyl)-benzofuran

Procedure

A mixture of 17.4 g. (0.1 mol.) of 2-n-butyl-benzofuran and 19.1 g. (0.1 mol.) of 4-acetoxy-3-methoxy-benzonitrile in 20 ml. of trifluoroacetic acid is refluxed for three hours. The reaction mixture is cooled, diluted with 200 ml. of water and the resulting aqueous solution is extracted with ether. The extracts are concentrated to dryness and the residue is dissolved in 100 ml. of ethanol and heated with 20 ml. of 10% aqueous sodium carbonate for two hours. The mixture is concentrated, the residue extracted with ether and the extracts are dried and concentrated in vacuo to give 2-n-butyl-3-(3'-methoxy-4'-hydroxybenzoyl)-benzofuran.

Workup

  1. additionA mixture of 17.4 g
  2. temperatureThe reaction mixture is cooled
  3. additiondiluted with 200 ml
  4. extractionof water and the resulting aqueous solution is extracted with ether
  5. concentrationThe extracts are concentrated to dryness
  6. dissolutionthe residue is dissolved in 100 ml
  7. temperatureof ethanol and heated with 20 ml
  8. concentrationThe mixture is concentrated
  9. extractionthe residue extracted with ether
  10. customthe extracts are dried
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ffe1b58ec9224d559e9287ac0a280d4f
Source dataset
uspto-grants-1976_08
Patent number
US03975537

Reaction notes

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