Sodium Hydroxide → 4-Methanesulfonyloxy-benzenesulfonic acid sodium salt

HRID 1261183Notes

Reaction equation

HRID 1261183 reaction equation
O.O.[Na+:3].[OH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([O-:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1.[OH-].[Na+].[CH3:17][S:18](Cl)(=[O:20])=[O:19]>O.[Cl-].[Na+].O>[Na+:3].[CH3:17][S:18]([O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([O-:14])(=[O:12])=[O:13])=[CH:7][CH:6]=1)(=[O:20])=[O:19]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 23666329Sodium P-phenolsulfonate dihydrate

Product 1

HCID 593896784-Methanesulfonyloxy-benzenesulfonic acid sodium saltYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

4-Hydroxybenzenesulfonic acid sodium salt dihydrate (11.6 g, 50.0 mmol) and sodium hydroxide (2.00 g, 50.0 mmol) were dissolved in distilled water (50 mL) and the solution cooled to 0° C. Methane sulfonyl chloride (4.25 mL, 55.0 mmol) was added dropwise with stirring and the mixture then allowed to warm to room temp. and left for 2 h. Brine (20 mL) was added and the solution left to stand for 1 h with the formation of white crystalline solid. The solids were filtered, recrystallised (brine), and dried under vacuum to give the title compound as a white crystalline solid (7.81 g, 57%),

Workup

  1. temperatureto warm to room temp.
  2. waitthe solution left
  3. waitto stand for 1 h with the formation of white crystalline solid
  4. filtrationThe solids were filtered
  5. customrecrystallised (brine)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-18d258ffe71e49d6a41459009f4b28c6
Source dataset
uspto-grants-2013_06
Patent number
US08470860B2

Reaction notes

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