2,4-Di-tert-butylphenol → HCID 22648340, compound

HRID 393969Notes

Reaction equation

HRID 393969 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1.[C:16]([C:20]1[CH:25]=[C:24]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:23]=[CH:22][C:21]=1[OH:30])([CH3:19])([CH3:18])[CH3:17]>C1(C)C=CC=CC=1>[C:16]([C:20]1[CH:25]=[C:24]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:23]=[C:22]([CH:12]([C:11]2[CH:14]=[CH:15][C:8]([F:7])=[CH:9][CH:10]=2)[N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:21]=1[OH:30])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 73112,4-Di-tert-butylphenolHCID 8082PiperidineHCID 680234-Fluorobenzaldehyde

Product 1

HCID 22648340HCID 22648340, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

8.29 g (97.33 mmol) of piperidine are added, at room temperature, to a solution of 5.52 g (44.43 mmol) of 4-fluorobenzaldehyde in 50 ml of toluene. The slightly yellow-colored solution is boiled under reflux for 16 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 16 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 15.40 g (91%) of compound (205) (Table 2), m.p. 135-136° C. Molecular weight C26H36FNO (397.58). Analysis, calculated: C 78.55; H 9.13; N 3.52%. Analysis, found: C 78.48; H 9.09; N 3.50%. 1HNMR (300 MHz, CDCl3, ppm): 1.12 (s, 9H); 1.37 (s, 9H); 1.57 (m, 4H); 2.28 (bm, 6H); 4.35 (s, 1H); 6.63 (d, 1H); 6.91 (dt, 2H); 7.08 (d, 1H); 7.32 (bm, 4H).

Workup

  1. temperatureunder reflux for 16 hours
  2. customapproximately 1 ml of water is separated off
  3. temperatureat reflux for further 16 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-ebf180d4021048d09a7efd1185c5065b
Source dataset
uspto-grants-2004_10
Patent number
US06809208B2

Reaction notes

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