4-Methoxybenzenesulfonyl chloride → Benzenesulfonic Acid

HRID 238216Notes

Reaction equation

HRID 238216 reaction equation
[OH:1]CCNCCO.CO[C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1>C1COCC1>[C:13]1([S:16]([OH:18])(=[O:1])=[O:17])[CH:14]=[CH:15][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8113Diethanolamine

Product 1

HCID 7371Benzenesulfonic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2-hydroxy-ethylamino)-ethanol (7 g, 67 mmol) and 4-methoxybenzenesulfonyl chloride (40 g, 194 mmol) in THF (400 mL) KOH (100 mL, 40%) was added dropwise at 0° C., after stirring over 3 hr the mixture was filtrated and THF was evaporated in vacuo, then extracted with EtOAc (500 mL). The organic layer was washed with brine and dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column to afford Benzenesulfonic acid, 4-methoxy-, [[(4-methoxyphenyl)sulfonyl]imino]di-2,1-ethanediyl ester as a colorless gum (20 g, 49%). 1H NMR (DMSO-d6) δ 7.81 (d, J=4.8 Hz, 4H), 7.79 (d, J=5.2 Hz, 2H), 7.01 (d, J=4.8 Hz, 4H), 6.93 (d, J=5.2 Hz, 2H), 4.08 (t, J=6 Hz, 4H), 3.88 (s, 6H), 3.86 (s, 3H), 3.35 (t, J=6 Hz, 4H). MS (ESI) m/z (M+1)+: 615.7.

Workup

  1. filtrationwas filtrated
  2. customTHF was evaporated in vacuo
  3. extractionextracted with EtOAc (500 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-aca49454d4514b68b1b1e2d467308679
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

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