Trifluoroacetic acid → 3-(3-Methoxy-4-hydroxybenzoyl)-2-phenylbenzofuran

HRID 2398484Notes

Reaction equation

HRID 2398484 reaction equation
[C:1]1([C:7]2[O:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O:19][C:20]1[CH:27]=[CH:26][C:23]([C:24]#N)=[CH:22][C:21]=1[O:28][CH3:29])(=O)C.FC(F)(F)C(O)=[O:33]>>[CH3:29][O:28][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:20]=1[OH:19])[C:24]([C:11]1[C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[O:8][C:7]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:33]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7937734-Cyano-2-methoxyphenyl acetateHCID 35179362-Phenyl-benzofuran

Product 1

HCID 214352623-(3-Methoxy-4-hydroxybenzoyl)-2-phenylbenzofuran

Procedure

A mixture of 19.4 g. (0.1 mol.) of 2-phenylbenzofuran and 19.1 g. (0.1 mol.) of 4-acetoxy-3-methoxybenzonitrile 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 to give 3-(3-methoxy-4-hydroxybenzoyl)-2-phenylbenzofuran.

Workup

  1. additionA mixture of 19.4 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

Sources & evidence

ORD record
ord-516b9a3fe1c5438f8d499e7b3ca6cbb3
Source dataset
uspto-grants-1977_05
Patent number
US04024273

Reaction notes

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