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

HRID 1106994Notes

Reaction equation

HRID 1106994 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[OH-].[CH2:17]([N+:21]([CH2:30][CH2:31][CH2:32][CH3:33])([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH3:20]>C1(C)C=CC=CC=1.CO>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[O-:15])([CH3:4])([CH3:3])[CH3:2].[CH2:30]([N+:21]([CH2:17][CH2:18][CH2:19][CH3:20])([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:26][CH2:27][CH2:28][CH3:29])[CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 2

HCID 314052,6-Di-tert-butylphenolHCID 2723671Tetrabutylammonium Hydroxide

Product 1

HCID 9911496Tetrabutylammonium 2,6-di-t-butylphenoxide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

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).

Workup

  1. stirringThe resulting dark green solution was stirred for 1 hour
  2. concentrationconcentrated under vacuum to a thick residue
  3. additionTwo 100 mL portions of toluene were added
  4. customremoved by evaporation under vacuum

Sources & evidence

ORD record
ord-72d5d51b13a74a1cb519451895669344
Source dataset
uspto-grants-2000_05
Patent number
US06057455

Reaction notes

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