Abstract
A facile conversion of aromatic aldehydes to esters using molecular sieves, TS-1, and 30% H2 O2 is described.
Keywords
oxidation - aldehyde - carboxylic acid
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27
Typical Procedure for the Preparation of Dimethyl Terephthalate : In a typical reaction, 0.56 mL aq solution of H2 O2 (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 Na2 SO4 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).
