4-tert-Butylphenol → 4-tert-Butylphenol sodium salt

HRID 1662169Notes

Reaction equation

HRID 1662169 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+:13]>>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O-:11])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3].[Na+:13]

Participants

3

Reactant 2

HCID 73934-tert-Butylphenol3×HCID 14798Sodium Hydroxide

Product 1

HCID 236680594-tert-Butylphenol sodium saltYield 81%

Procedure

4-tert-Butylphenol (27.6 g, 0.184 mol) was charged into 2 L three-necked round bottom flask equipped with a mechanical stirrer, a dropping funnel, and a condenser. The flask was purged with nitrogen gas, and 184 mL of 1N aqueous sodium hydroxide solution added to the flask. Additionally, 47 mL of water was added into the solution. The stirred reaction mixture was heated at 50° C. until 4-tert-butylphenol was completely dissolved. In this way, 4-tert-butylphenol was reacted with sodium hydroxide to form sodium 4-tert-butylphenolate. The solution of sodium 4-tert-butylphenolate in water was then cooled to 20° C. and 100 mL of dichloromethane added to the solution. The organic layer obtained in step 2, which contained 0.0835 mole of the perfluorobutane-1,4-di(sulfonyl halides), was dropwise added to the reaction mixture for 2 hours. The reaction mixture was stirred at 20° C. for 12 hours and transferred to a separatory funnel. The upper water layer was separated from the lower organic (dichloromethane) layer. The water layer was then washed using 100 mL of ethyl acetate. The water layer was 274 g. 19F-NMR analysis (using hexafluoroglutaric acid as a reference) showed that the water layer contained 0.068 mol of sodium perfluorobutane-1,4-di(sulfinate). The yield was 81%. 19F-NMR (in D2O); δ −122.67 (s, 4F, CF2), −130.12 (s, 4F, CF2) ppm.

Workup

  1. customequipped with a mechanical stirrer, a dropping funnel, and a condenser
  2. customThe flask was purged with nitrogen gas, and 184 mL of 1N aqueous sodium hydroxide solution
  3. additionadded to the flask
  4. additionAdditionally, 47 mL of water was added into the solution
  5. customThe stirred reaction mixture
  6. dissolutionwas completely dissolved

Sources & evidence

ORD record
ord-74bbcb87a051413894182b56a4c25813
Source dataset
uspto-grants-2011_10
Patent number
US08030516B2

Reaction notes

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