Phenol → Benzenesulfonic acid, phenyl ester

HRID 1742551Notes

Reaction equation

HRID 1742551 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]1([OH:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:1]1([S:7]([O:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 996PhenolHCID 7369Benzenesulfonyl chloride

Product 1

HCID 78064Benzenesulfonic acid, phenyl esterYield 81%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

All apparatus is rigorously dried and flushed with nitrogen before use. The reaction is performed in a 25 ml flask equipped with a magnetic stirring bar and a calcium chloride drying tube. The flask is charged with benzenesulfonyl chloride (11.60 g, 65.7 mmol), phenol (5.60 g, 59.6 mmol), and 4-dimethylaminopyridine (0.36 g, 2.98 mmol), and anhydrous pyridine (20 ml). The reaction mixture is stirred and heated at reflux, and the progress of the reaction is monitored by high performance liquid chromatography. At the conclusion of the reaction, the mixture is cooled and quenched with water (25 ml), extracted with ether (50 ml), and washed successively with 50 ml portions of water, 5% sodium hydroxide (2×), water, and brine. The organic phase is then dried over magnesium sulphate, filtered, and concentrated to yield 13.1 g (94%) of the crude product as a yellow oil. This product is further purified by distillation on a Kugelrohr apparatus under vacuum to give 11.3 g (81%) of the product as a colorless oil. The oxidative stability of the product is determined by pressure differential scanning calorimetry (PDSC). The results are reported below in Table 1.

Workup

  1. customAll apparatus is rigorously dried
  2. customflushed with nitrogen before use
  3. customThe reaction is performed in a 25 ml flask
  4. customequipped with a magnetic stirring bar and a calcium chloride drying tube
  5. temperatureheated
  6. temperatureat reflux
  7. customAt the conclusion of the reaction
  8. temperaturethe mixture is cooled
  9. customquenched with water (25 ml)
  10. extractionextracted with ether (50 ml)
  11. washwashed successively with 50 ml portions of water, 5% sodium hydroxide (2×), water, and brine
  12. dry with materialThe organic phase is then dried over magnesium sulphate
  13. filtrationfiltered
  14. concentrationconcentrated
  15. customto yield 13.1 g (94%) of the crude product as a yellow oil
  16. distillationThis product is further purified by distillation on a Kugelrohr apparatus under vacuum

Sources & evidence

ORD record
ord-3d3feb870b114efaaf5c735c1900ae7c
Source dataset
uspto-grants-1994_08
Patent number
US05340489

Reaction notes

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