Trimethyl cis,cis-1,3,5-cyclohexanetricarboxylate

Used as Organic Building Blocks.

A mixture of 7.50 g (3.57 mmol) of trimesic acid, 1.0 g of 5% rhodium on alumina, and 150 mL of water was hydrogenated at 70 °C and 50 psi of H2. Uptake was complete in 48 h, and the filtrate was concentrated to give a white solid. Recrystallization from a 1:4 mixture of ethanol/toluene gave 4.50 g (20.8 mmol) of the Trimethyl cis,cis-1,3,5-cyclohexanetricarboxylate. Yield 58%. 1H NMR(500 MHz, CD3OD): δ 12.22 (br, 3H; 3COOH), 2.32 (tt, J= 3, 13 Hz; 3H, 3Hax′), 2.04 (d, J= 13 Hz, 3H; 3Heq), 1.19 (q, J= 13 Hz, 3H; 3Hax).