2,4-Di-tert-butylphenol → HCID 22648343, compound

HRID 393971Notes

Reaction equation

HRID 393971 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7]([C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1)#[N:8].[C:17]([C:21]1[CH:26]=[C:25]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:24]=[CH:23][C:22]=1[OH:31])([CH3:20])([CH3:19])[CH3:18]>C1(C)C=CC=CC=1>[C:17]([C:21]1[CH:26]=[C:25]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:24]=[C:23]([CH:13]([C:12]2[CH:15]=[CH:16][C:9]([C:7]#[N:8])=[CH:10][CH:11]=2)[N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:22]=1[OH:31])([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 73112,4-Di-tert-butylphenolHCID 8082PiperidineHCID 660424-Cyanobenzaldehyde

Product 1

HCID 22648343HCID 22648343, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

8.29 g (97.33 mmol) of piperidine are added, at room temperature, to a solution of 5.83 g (44.43 mmol) of 4-cyanobenzaldehyde 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 6 hours and then cooled to room temperature; the solvent is distilled off using a vacuum rotary evaporator. Crystallisation of the residue from methanol yields 12.95 g (75%) of compound (206) (Table 2), m.p. 165-166° C. Molecular weight C27H36N2O (404.60). Analysis, calculated: C 80.15; H 8.97; N 6.92%. Analysis, found: C 80.01; H 9.00; N 6.78%. 1HNMR (300 MHz, CDCl3, ppm): 1.12 (s, 9H); 1.36 (s, 9H); 1.57 (m, 4H); 2.28 (bm, 6H); 4.34 (s, 1H); 6.63 (d, 1H); 7.09 (d, 1H); 7.51 (m, 4H).

Workup

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

Sources & evidence

ORD record
ord-f9ea4dadcc814ec399af68eaef1ecfd3
Source dataset
uspto-grants-2004_10
Patent number
US06809208B2

Reaction notes

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