Methanol → Methyl 2,4,6-trimethylbenzene-1-sulfonate

HRID 2173894Notes

Reaction equation

HRID 2173894 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10](Cl)(=[O:12])=[O:11].[OH-:14].[Na+].[CH3:16]O>>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10]([O:12][CH3:16])(=[O:14])=[O:11]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 130462-Mesitylenesulfonyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 13310198Methyl 2,4,6-trimethylbenzene-1-sulfonateYield 96%

Procedure

to a solution of 2,4,6-trimethylbenzene-1-sulfonyl chloride (30 g, 0.136 mol) dissolved in methanol (350 ml), a solution of NaOH (5.49 g, 0.136 mol, 1 equiv.) dissolved in methanol (60 ml) was added dropwise. White NaCl was precipitated and filtered to remove NaCl, and the filtered solution was evaporated, followed by extraction with water and methylene chloride, and the organic layer was obtained, evaporated the solvent therefrom and then dried in a vacuum, affording a white solid at a yield of 96%.

Workup

  1. additionwas added dropwise
  2. customWhite NaCl was precipitated
  3. filtrationfiltered
  4. customto remove NaCl
  5. customthe filtered solution was evaporated
  6. extractionfollowed by extraction with water and methylene chloride
  7. customthe organic layer was obtained
  8. customevaporated the solvent
  9. customdried in a vacuum
  10. customaffording a white solid at a yield of 96%

Sources & evidence

ORD record
ord-7c0eebe1760e4946aaf165df84aa45b7
Source dataset
uspto-grants-2015_06
Patent number
US09057929B2

Reaction notes

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