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

Abstract

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

Keywords

oxidation - aldehyde - carboxylic acid

References

• 1 Corey EJ. Gilman NW. Ganem BE. J. Am. Chem. Soc.  1968,  90:  5616 
• 2 Craig JC. Horning EC. J. Org. Chem.  1960,  25:  2098 
• 3 Mavel EN. Joncich MJ. J. Am. Chem. Soc.  1951,  73:  973 
• 4 Elad D. Youssefyeh RD. Tetrahedron Lett.  1963,  2189 
• 5 Abiko A. Roberts JC. Takemasa T. Masamune S. Tetrahedron Lett.  1986,  27:  4537 
• 6 O’Connor B. Just G. Tetrahedron Lett.  1987,  28:  3235 
• 7 Thomason SC. Kubler DG. J. Chem. Educ.  1968,  45:  546 
• 8 Rajendran S. Trivedi DC. Synthesis  1995,  153 
• 9 Grigg R. Mitchell TRB. Sutthivaiyakit S. Tetrahedron  1981,  37:  4313 
• 10 Yamada S. Morizono D. Yamamoto K. Tetrahedron Lett.  1992,  33:  4329 
• 11 Dalcanale E. Montanari F. J. Org. Chem.  1986,  51:  567 
• 12 McDonald C. Holcomb H. Kennedy K. Kirkpatrick E. Leathers T. Vanemon P. J. Org. Chem.  1989,  54:  1213 
• 13 Okimoto M. Chiba T. J. Org. Chem.  1988,  53:  218 
• 14a Gopinath R. Patel BK. Org. Lett.  2000,  2:  577 
• 14b Sato K. Hyodo M. Takagi J. Aoki M. Noyori R. Tetrahedron Lett.  2000,  41:  1439 
• 15
• 16 Thangaraj A. Kumar R. Mirajkar SP. Ratnasamy P. J. Catal.  1991,  130:  1 
• 17 Reddy JS. Kumar R. J. Catal.  1991,  130:  140 
• 18 Sheldon RA. Top. Curr. Chem.  1993,  164:  21 
• 19 Kumar P. Kumar R. Pandey B. Synlett  1995,  289 
• 20 Murugavel R. Roesky HW. Angew. Chem. Int. Ed. Engl.  1997,  36:  477 
• 21 Reddy RS. Reddy JS. Kumar R. Kumar P. J. Chem. Soc., Chem. Commun.  1992,  84 
• 22 Sonawane HR. Pol AV. Moghe PP. Biswas SS. Sudalai A. J. Chem. Soc., Chem. Commun.  1994,  1215 
• 23 Joseph R. Sudalai A. Ravindranathan T. Tetrahedron Lett.  1994,  35:  5493 
• 24 Huybrechts DRC. De Bruycker L. Jacobs PA. Nature  1990,  345:  240 
• 25 Tatsumi T. Nakamura M. Nagishi S. Taminaga H. J. Chem. Soc., Chem. Commun.  1990,  476 
• 26 Shinohara H, and Ohashi H. inventors; Japanese Patent  7303833.  ; Chem. Abstr., 1973, 79, P42176y

27

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).