Toluene → 2,4-Di-tert-butyl-6-[piperidin-1-yl-(4-trifluoromethyl-phenyl)-methyl]-phenol

HRID 393967Notes

Reaction equation

HRID 393967 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:7][C:8]([C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1C=O)([F:10])[F:9].[C:19]([C:23]1[CH:28]=[C:27]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:26]=[CH:25][C:24]=1[OH:33])([CH3:22])([CH3:21])[CH3:20].[C:34]1(C)C=CC=CC=1>>[C:19]([C:23]1[CH:28]=[C:27]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:26]=[C:25]([CH:34]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:16]2[CH:15]=[CH:12][C:11]([C:8]([F:7])([F:9])[F:10])=[CH:18][CH:17]=2)[C:24]=1[OH:33])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 4

HCID 1140Toluene2×HCID 73112,4-Di-tert-butylphenolHCID 8082PiperidineHCID 123067o-(Trifluoromethyl)benzaldehyde

Product 1

HCID 226483422,4-Di-tert-butyl-6-[piperidin-1-yl-(4-trifluoromethyl-phenyl)-methyl]-phenolYield 79%

Procedure

8.29 g (97.33 mmol) of piperidine are added, at room temperature, to a solution of 7.74 g (44.43 mmol) of trifluoromethylbenzaldehyde in 50 ml of toluene. The slightly yellow-colored solution is boiled under reflux for 4 hours; approximately 1 ml of water is separated off using a water separator, and a solution of 8.73 g (42.32 mmol) of 2,4-di-tert-butylphenol in 15 ml of toluene is then added dropwise. The reaction mixture is boiled at reflux for further 17 hours and then cooled to room temperature; the solvent is distilled off using a vacuum rotary evaporator. Crystallisation of the residue from iso-propanol/methanol (1:1) yields 15.04 g (79%) of compound (201) (Table 2), m.p. 150-152° C. Molecular weight C27H36F3NO (447.59). Analysis, calculated: C 72.45; H 8.11; N 3.13%. Analysis, found: C 72.63; H 8.05; N 3.05%. 1HNMR (300 MHz, CDCl3, ppm): 1.12 (s, 9H); 1.39 (s, 9H); 1.56 (m, 4H); 2.28 (bm, 6H); 4.37 (s, 1H); 6.65 (d, 1H); 7.08 (d, 1H); 7.47 (m, 4H).

Workup

  1. temperatureunder reflux for 4 hours
  2. customapproximately 1 ml of water is separated off
  3. temperatureat reflux for further 17 hours
  4. distillationthe solvent is distilled off
  5. customa vacuum rotary evaporator
  6. customCrystallisation of the residue from iso-propanol/methanol (1:1)

Sources & evidence

ORD record
ord-6c21811a693748b0a090d5f1d69c7d99
Source dataset
uspto-grants-2004_10
Patent number
US06809208B2

Reaction notes

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