P-Cresol → Sodium p-methylphenolate

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+:10]>C1COCC1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O-:8])=[CH:4][CH:3]=1.[Na+:10]

Participants

Procedure

4-methylphenol (3.73 g, 0.035 mol) is dissolved in 10 mL THF and added dropwise to a suspension of sodium hydride (0.83 g, 0.035 mol) in 60 mL THF to produce sodium 4-methyl phenoxide. HOC6H4SO2NNaSO2CF3 (4.06 g, 0.012 mol) is dissolved in 50 mL THF and added dropwise to a suspension of sodium hydride (0.30 g, 0.012 mol) and tetra(n-butyl)ammonium bromide (0.4 g) in 50 mL THF and stirred for 16 hours to produce a sodium phenoxide solution of the sulfonimide NaOC6H4SO2NNaSO2CF3.