Uses
Methyl 3,5-dimethylbenzoate may be used in the preparation of four carbon isostere related to highly active 4-pyridinemethanols, which were subsequently evaluated for their antimalarial activity. It may be used in the total synthesis of (±)-indoxamycin B.
General Description
Methyl 3,5-dimethylbenzoate is an aromatic carboxylic acid ester. It was selected as ligand during monomer screening for the synthesis and investigation of various europium compounds containing pinacolyl methylphosphonate with different ligands. Methyl 3,5-dimethylbenzoate is reported as precursor of methyl-3,5-divinylbenzoate.
Synthesis
Bromobenzene (0.125 g, 0.0081 mol) and 10% palladium carbon (50% wet, 0.2 g) were added to an autoclave with 3,5-dimethylbenzoic acid (1.0 g, 0.0081 mol) and methanol (3 mL). The autoclave was pressurized with nitrogen (1-2 bar) followed by the addition of hydrogen (1-2 bar) and adjusted to the desired hydrogen pressure (5-6 bar). The reaction mixture was heated to 55-60 °C and stirred at 300 rpm for 4 hours. Upon completion of the reaction, the catalyst was filtered through a bed of diatomaceous earth to remove the catalyst. Water (30 mL) was added to the filtrate and the reaction mixture was extracted with isopropyl acetate (2 x 15 mL). The organic layers were combined, washed with 5% aqueous sodium bicarbonate (2 × 15 mL), dried over anhydrous Na2SO4 and filtered. Finally, the filtrate was evaporated by vacuum to give methyl 3,5-dimethylbenzoate product.
References
[1] Helvetica Chimica Acta, 1996, vol. 79, # 7, p. 1967 - 1979
[2] Journal of Organic Chemistry, 2006, vol. 71, # 19, p. 7205 - 7213
[3] Monatshefte fur Chemie, 1996, vol. 127, # 2, p. 185 - 200
[4] European Journal of Organic Chemistry, 2009, # 26, p. 4480 - 4485
[5] Tetrahedron Letters, 2013, vol. 54, # 42, p. 5690 - 5694
