Phosphoric Acid → 2',3',4',5'-Tetrahydro-[1,1'-biphenyl]-4-amine

Participants

Reaction Steps

This compound was prepared similarly as described in J. v. Braun et al., J. Liebigs Ann. Chem., 472 (1929), 1-89, from refluxing aniline (2 equivalents), cyclohexanone (1 equivalent) in ethanol and 37% hydrochloric acid for 4-5 days, followed by addition of ethyl acetate, water, and sodium hydroxide, neutralisation with 85% phosphoric acid, phase separation, and distillation of the organic phase. The residue was added a catalytic amount of sulfuric acid and distilled (180° C., 5-7 mbar). The distillate was redistilled (120° C., 3 mbar) to afford (in the residue) a 49% yield of the desired 4-cyclohex-1-enylaniline.

Provenance & Evidence