Dicyclohexylamine → HCID 70014764, compound

HRID 1018970Notes

Reaction equation

HRID 1018970 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C1(NC2CCCCC2)CCCCC1.[P:28]([O-:33])([O:31]C)[O:29][CH3:30]>CC(C)=O>[CH3:30][O:29][P:28]([OH:33])([O:14][CH3:11])=[O:31].[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7582DicyclohexylamineHCID 13827894-(4-Methylphenyl)phenolHCID 21884954Dimethylphosphite

Product 1

HCID 70014764HCID 70014764, compoundYield 188.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4′-methyl-4-hydroxybiphenyl (4.3 g, 23.4 mmol) and dicyclohexylamine (5.2 mL, 26.1 mmol) in acetone (30 mL) was refluxed for 1 h. Solvent was then evaporated in vacuo. The residue was dissolved in CCl4 (120 mL) and mixed with dimethyl phosphite (2.4 mL, 26.2 mmol). The mixture was refluxed for 4 h., cooled to r.t. and filtered. The filtrate was concentrated and chromatographed over silica gel eluting with hexanes:EtOAc (2:3) to give 6.5 g (95%) of the title compound as a white solid.

Workup

  1. temperaturewas refluxed for 1 h
  2. customSolvent was then evaporated in vacuo
  3. dissolutionThe residue was dissolved in CCl4 (120 mL)
  4. temperatureThe mixture was refluxed for 4 h.
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customchromatographed over silica gel eluting with hexanes:EtOAc (2:3)

Sources & evidence

ORD record
ord-7c55e58582b245cc8a3427b807809f48
Source dataset
uspto-grants-2002_11
Patent number
US06486141B2

Reaction notes

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