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

Participants

Reaction Steps

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).

Provenance & Evidence