Bodroux, Daniel published the artcileSyntheses in the phenylcyclohexane series, COA of Formula: C13H16O2, the publication is Bulletin de la Societe Chimique de France (1939), 1411-16, database is CAplus.
The reaction mixture obtained by the dropwise addition of 160 g. Br to 160 g. of phenylcyclohexane (I) containing 16 g. of powd. I was washed with 10% NaOH and water, and steam distilled, yielding 190 g. of p-bromocyclohexylbenzene (II), b10 153-5°, d418 1.288, nD18 1.5645, M. R. 60.4 (calculated 59.82), oxidized by CrO3 in AcOH to the corresponding p-BrC6H4CO2H, m. 250-1°. The Grignard reagent (III) from 48 g. II, 5 g. Mg and 80 g. Et2O was treated with solid CO2 and after decomposition with dilute HCl gave 25 g. of p-cyclohexylbenzoic acid, m. 197°, oxidized by KMnO4 in 10% boiling KOH to terephthalic acid, m. 310-20°, identified through its mononitro derivative Hydrolysis of the acetal obtained by the action of HC(OEt)3 on II in Et2O yielded 53% of p-cyclohexylbenzaldehyde (IV), b10 158-9°, d420 1.028, nD20 1.524, M. R. 55.96 (calculated 56.73). Passage of a steady current of dry HCl through a well-stirred mixture of 320 g. I, 40 g. powd. ZnCl2 and 30 g. paraformaldehyde produced 160 g. (77%) of p-cyclohexylbenzyl chloride (V), b12 162-4°, d412 1.071, nD12 1.5525, M. R. 62.31 (calculated 61.50), converted by continual agitation with boiling solutions of Cu(NO3)2 or Pb(NO3)2 to 22% and 34% of IV; PhNH2 addition compound, C19H21N, m. 117-18°. Oxidation of the Grignard reagent (VI) from V by a current of air free from CO2 gave 34% of p-cyclohexylbenzyl alc. (VII), m. 40°. Conversion of V to the corresponding acetate, m. 48°, by boiling with NaOAc in AcOH and consequent saponification gave 50% of VII, oxidized by boiling 5% HNO3 to 83% of the corresponding acid. Treatment of VI with CO2 gave 60% of p-cyclohexylphenylacetic acid, m. 78.5°, oxidized by KMnO4 to terephthalic acid. Treatment of VI with HC(OEt)3 did not give the corresponding acetal. In the preparation of III, 1% of bis(p-cyclohexyl)biphenyl, m. 202-3°, was formed. Refluxing V in Et2O with Na gave bis(p-cyclohexyl)bibenzyl (VIII), m. 148-9°, in 65% yields. VIII was also formed in 17% yields in the preparation of VI.
Bulletin de la Societe Chimique de France 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, COA of Formula: C13H16O2.
Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider