2,6-Di-tert-butylphenol → Tetrabutylammonium 2,6-di-t-butylphenoxide

Participants

Reaction Steps

A solution of 22.69 g (110 mmol, 1.1 equivalents) of 2,6-di-t-butylphenol in 10 mL of toluene was treated with 100 mL (100 mmol) of a 1M solution of tetrabutylammonium hydroxide in methanol under nitrogen with stirring at ambient temperature. The resulting dark green solution was stirred for 1 hour and concentrated under vacuum to a thick residue. Two 100 mL portions of toluene were added and removed by evaporation under vacuum yielding 52.08 g of wet, crude title compound as a green solid which was used in the next step without further purification. 1H NMR (CDCl3) δ 7.13 (d, J=9 Hz, 2H), 6.77 (t, J=9 Hz, 1H), 3.30 (m, 8H), 1.61 (m, 8H), 1.41 (s, 18H), 1.40 (m, 8H), 0.96 (t, J=7 Hz, 12H).

Provenance & Evidence