Chemical Properties
Relative density 1.005, melting point 108-111°C, boiling point 134-136°C (15mmHg), refractive index 1.4598.
Uses
4-Methyl-1-cyclohexanecarboxylic acid was used to investigate the palladium core-porous silica shell-nanoparticles catalyzed hydrogenation of 4-carboxybenzaldehyde (4-CBA) to
p-toluic acid. It was also used in the synthesis of substituted cyclohexyl carbonyl chlorides.
Synthesis
GENERAL STEPS: The hydrogenation reaction was carried out in a 25 mL stainless steel autoclave with a PTFE liner. In a typical experiment, 20 mg of catalyst and 61 mg (0.5 mmol) of p-toluic acid were dispersed in 5 mL of deionized water. After sealing the autoclave, the air in the autoclave was replaced with hydrogen and pressurized to 2.5 MPa. Subsequently, the reaction mixture was heated to 110 °C under magnetic stirring (1000 rpm). Upon completion of the reaction, it was cooled to room temperature, the reaction mixture was extracted with ethyl acetate and separated by centrifugation to remove the solid catalyst. The recovered solid catalyst was washed sequentially with ethyl acetate, ethanol and deionized water. The filtrate was analyzed by gas chromatography (GC, HP5890, USA) equipped with a 30 m HP-5 capillary column and a flame ionization detector (FID). All products were confirmed structurally by gas chromatography-mass spectrometry (GC-MS, Agilent 6890).
References
[1] Tetrahedron Letters, 2004, vol. 45, # 35, p. 6669 - 6672
[2] Steroids, 1983, vol. 41, # 3, p. 349 - 359
[3] Recueil des Travaux Chimiques des Pays-Bas, 1961, vol. 80, p. 595 - 607
[4] Journal of the Chemical Society, 1937, p. 2003,2007
