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

HRID 268384Notes

Reaction equation

HRID 268384 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 3 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 2 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-d2b8d70c158b401295ed7179f4939b08
Source dataset
uspto-grants-1976_03
Patent number
US03947470

Reaction notes

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