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

Participants

Reaction Steps

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).

Provenance & Evidence