Water → Potassium 2,4-di-tert-butylphenolate

HRID 1703150Notes

Reaction equation

HRID 1703150 reaction equation
[OH-].[K+:2].[C:3]([C:7]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:10]=[CH:9][C:8]=1[OH:17])([CH3:6])([CH3:5])[CH3:4].O>C1(C)C=CC=CC=1>[C:3]([C:7]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:10]=[CH:9][C:8]=1[O-:17])([CH3:6])([CH3:5])[CH3:4].[K+:2]

Participants

5

Reactant 3

HCID 962Water2×HCID 73112,4-Di-tert-butylphenolHCID 14797Potassium Hydroxide

Product 1

HCID 23663687Potassium 2,4-di-tert-butylphenolate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4.85 grams of 46.3% aqueous potassium hydroxide was added to a solution of 8.24 grams of 2,4-di-tert.butylphenol in 250 ml of toluene and heated at reflux over a period of about 2 hours until all the water including reaction water was removed by azeotropic distillation yielding a dispersion of the potassium 2,4-di-tert. butylphenolate in toluene. To this dispersion at -5° C. was added a solution of 21.7 grams of the compund of Example 1 in 60 ml of toluene at -5° to -3° C. over a period of 25 minutes and then stirring continued overnight. The reaction mixture was clarified by filtration of the precipitated potassium chloride and the product isolated as a residue by distillation of the toluene at reduced pressures. The product was isolated as crystals after crystallization from a solvent mixture of acetonitrile and toluene yielding white crystals melting at 195°-197° C.

Workup

  1. temperatureheated
  2. temperatureat reflux over a period of about 2 hours until all
  3. customwas removed by azeotropic distillation

Sources & evidence

ORD record
ord-70327406587f42bc8519b6ca054186e1
Source dataset
uspto-grants-1982_09
Patent number
US04351759

Reaction notes

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