Mayes, Horace A. published the artcileNitration of phenylcyclohexane and of its p-halogen derivatives, Category: quinuclidine, the publication is Journal of the Chemical Society (1929), 500-8, database is CAplus.
Cyclohexyl chloride (62 g.), 160 g. PhCl and 14 g. AlCl3 give 74 g. p-chlorophenylcyclohexane (I), b10 134°, b15 140°, b19 145°, d425 1.065, nD25, 1.5386. Oxidation gives p-ClC6H4-CO2H. The p-Br derivative (II), b23 160°, d425 1.283, nD25 1.5584, results similarly in 65% yield. The p-NH2: derivative, through diazo reaction, gives the p-I derivative (III), b21 185°’, b11 174°, d419 1.448, nD25 1.5900. Nitration of phenyleyclohexane in AcOH at 0° gives 62.2% of the p-NO2 derivative, m. 57.5-8.5°; the o-NO2 derivative, b10 174°, d423 1.111, nD26 1.5472. With HNO3 (d. 1.5) at 0° there results the p-NO2 derivative and the 2,4-di-NO2 derivative, pale yellow, m. 57°. p-Aminophenylcyclohexane, m. 55°, results almost quant. by reducing with Fe and very dilute HCl; Ac derivative, m. 129°; 2-NO2 derivative, yellow, m. 65°, reduced to the 2,4-di-NH2 derivative, m. 108° (Ac derivative, m. 268°). I, added to 8 times its weight of HNO3 (d. 1.5) at 0° to -5°, gives the 2,5-di-NO2 derivative (IV), m. 92°; 4-piperidino derivative, orange-yellow, m. 108°. Nitration of I in AcOH at 5-10° gives about 56% of the 3-NO2 derivative Nitration of II gives 38% of the 3-NO2 compound III and HNO3 give p-IC6H4NO2. p-Acetylphenylcyclohexane, m. 68-9°, in 60% yield from phenylcyclohexane, AcCl, AlCl3 and CS2; phenylhydrazone, yellow, m. 105°. Oxidation gives p-cyclohexylbenzoic acid, m. 109° (Na salt, needles). Reduction of IV gives 4-chloro-2,5-diaminophenylcyclohexane, m. 95-6°.
Journal of the Chemical Society published new progress about 20029-52-1. 20029-52-1 belongs to quinuclidine, auxiliary class Carboxylic acid,Benzene, name is 4-Cyclohexylbenzoic acid, and the molecular formula is C13H16O2, Category: quinuclidine.
Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider