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

HRID 49541Notes

Reaction equation

HRID 49541 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]1(=O)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[OH-].[Na+].P(=O)(O)(O)O.S(=O)(=O)(O)O>C(O)C.Cl.O.C(OCC)(=O)C>[C:8]1([C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]=1

Participants

10

Reactant 5

HCID 1004Phosphoric AcidHCID 1118Sulfuric AcidHCID 6115AnilineHCID 7967CyclohexanoneHCID 14798Sodium Hydroxide

Product 1

HCID 126688602',3',4',5'-Tetrahydro-[1,1'-biphenyl]-4-amineYield 49%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  1. customThis compound was prepared similarly
  2. distillationdistilled (180° C., 5-7 mbar)
  3. distillationThe distillate was redistilled (120° C., 3 mbar)

Sources & evidence

ORD record
ord-1d62d3de1c54452eb24a36f49229e03f
Source dataset
uspto-grants-2004_03
Patent number
US06706744B2

Reaction notes

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