Sodium Hydroxide → HCID 86669856, compound

HRID 1627981Notes

Reaction equation

HRID 1627981 reaction equation
[CH3:1][S:2]([CH2:5][S:6]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:8])=[O:7])(=[O:4])=[O:3].[OH-].[Na+].[CH3:18][S:19](Cl)(=[O:21])=[O:20]>O>[CH3:1][S:2]([CH:5]([S:19]([CH3:18])(=[O:21])=[O:20])[S:6]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:7])=[O:8])(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 14971205HCID 14971205, compound

Product 1

HCID 86669856HCID 86669856, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

The above phenyl methylsulfonylmethanesulfonate (25 g, 0.1 mole) was dissolved in a solution of 75 mL of water and 8 g (0.1 mole) of 50% sodium hydroxide. The solution was cooled to 0-5° C. and treated with 11.4 g of methanesulfonyl chloride which was added dropwise over 45 min. The resulting slurry was filtered (starting material precipitates during the addition) and the solid (14.3 g after drying) was washed with 75 mL of water. The filtrate was treated with conc HCl until no more solid precipitated. The phenyl bis(methylsulfonyl)methanesulfonate product was filtered and washed with ice-water. After drying in a 60° C. vacuum oven the product (12.9 g, mp 154-156° C.) was recrystallized from ethyl acetate with a hot clarification to give 11.3 g, (34.4% conversion, 80% yield) of phenyl bis(methylsulfonyl)methanesulfonate as a white solid, mp 159-160° C. H1NMR: δ 7.36-7.44 (m, 5H); δ 2.65 (s, 6H). No major impurities were detected by HPLC-MS.

Workup

  1. additionwas added dropwise over 45 min
  2. filtrationThe resulting slurry was filtered (
  3. customprecipitates during the addition) and
  4. customthe solid (14.3 g after drying)
  5. washwas washed with 75 mL of water
  6. additionThe filtrate was treated with conc HCl until no more solid
  7. customprecipitated
  8. filtrationThe phenyl bis(methylsulfonyl)methanesulfonate product was filtered
  9. washwashed with ice-water
  10. dry with materialAfter drying in a 60° C. vacuum oven the product (12.9 g, mp 154-156° C.)
  11. customwas recrystallized from ethyl acetate with a hot clarification

Sources & evidence

ORD record
ord-848b2eec515d4ae4afbed4a27b58711e
Source dataset
uspto-grants-2014_07
Patent number
US08785686B2

Reaction notes

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