Titanosilicate (TS-1) Catalyzed Oxidation of Aromatic Aldehydes to Esters

 

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Abstract

A facile conversion of aromatic aldehydes to esters using molecular sieves, TS-1, and 30% H₂O₂ is described.

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Typical Procedure for the Preparation of Dimethyl Terephthalate: In a typical reaction, 0.56 mL aq solution of H₂O₂ (30%, 5 mmol) was added dropwise to a stirred solution of 0.134 g of terephthaldehyde (1 mmol) and TS-1 (10% by weight) in MeOH and the mixture refluxed until completion of reaction (8 h). The solvent was removed by evaporation and the residue washed with water and extracted with EtOAc. Drying over anhyd Na₂SO₄ and removal of solvent furnished 0.19 g essentially of pure diester in 99% yield. IR(nujol): 1710, 1680, 1440, 1370, 1260, 1190, 1100 cm^{-1 ¹} H NMR (200 MHz): δ = 3.95 (s, 6 H); 8.10 (s, 4 H) MS (m/e): 194(24) [M⁺], 179(5), 164(11), 163(100), 135(27), 120(9), 119(9), 104(17), 103(23), 77(19), 76(34), 75(23).