4-Formylbenzoic acid → 2-[4-(4-Carboxystyryl)phenyl]benzofuran

HRID 1283070Notes

Reaction equation

HRID 1283070 reaction equation
[C:1]1([CH3:16])[CH:6]=[CH:5][C:4]([C:7]2[O:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[CH:11]=2)=[CH:3][CH:2]=1.[C:17]([OH:27])(=[O:26])[C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1.CC(C)([O-])C.[K+]>CN(C)C=O>[C:17]([C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[CH:16][C:1]2[CH:2]=[CH:3][C:4]([C:7]3[O:8][C:9]4[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=4[CH:11]=3)=[CH:5][CH:6]=2)=[CH:20][CH:19]=1)([OH:27])=[O:26]

Participants

5

Reactant 3

HCID 120884-Formylbenzoic acidHCID 6384582-(p-Tolyl)benzofuranHCID 23665647Potassium tert-butoxide

Product 1

HCID 539534682-[4-(4-Carboxystyryl)phenyl]benzofuran

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Proceeding in a manner similar to that described in Example 1 above, 2-(p-tolyl)benzofuran (2.08 g; 0.01 mole) was interacted with 2.25 g (0.01 mole) of the anil derivative of terephthalaldehydic acid in the presence of 6.72 g (0.06 mole) of potassium tert-butoxide in 150 ml of dimethylformamide. The resulting product was purified by sublimation to obtain 2-[4-(4-carboxystyryl)phenyl]benzofuran which melted at 348°-349°C. The wavelength of maximum excitation of this compound was 365 nm and the wavelength of maximum emission was 425 nm.

Workup

  1. customThe resulting product was purified by sublimation

Sources & evidence

ORD record
ord-abcb3afc9ede44cb83c03fa924d0d6e1
Source dataset
uspto-grants-1976_08
Patent number
US03974144

Reaction notes

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