4-Toluenesulfonyl chloride → 2-(2-(2-Ethoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate

HRID 589247Notes

Reaction equation

HRID 589247 reaction equation
[OH-].[Na+].[CH2:3]([O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][OH:14])[CH3:4].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>O.C(Cl)Cl>[CH3:25][C:15]1[CH:20]=[CH:19][C:18]([S:21]([O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:3][CH3:4])(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8190Triethylene glycol monoethyl etherHCID 14798Sodium Hydroxide

Product 1

HCID 107353362-(2-(2-Ethoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

In a 3-neck, 2 L rbf, NaOH (135 g, 3.37 mol) was added slowly to water (1 L). After the addition was complete, the solution was cooled to room temperature and DCM (2 L) added, followed by triethylene glycol monoethyl ether (500 g, 2.81 mol). p-Toluenesulfonyl chloride (535 g, 2.81 mol) was added portion-wise over a period of 10 minutes, and the mixture refluxed for 2 hours. After cooling to room temperature, the reaction mixture was poured into water (2 L), mixed well and separated. The organic phase was washed with water (2×2 L), dried over MgSO4, filtered and solvent removed by rotary evaporation. The resulting clear, colourless oil was stirred at room temperature with a 10% aqueous NaOH solution (1 L) to hydrolyze unreacted p-toluenesulfonyl chloride. After 18 hours, the material was poured into water (1 L), extracted with chloroform (500 mL) and separated. The organic portion was washed with water (2 L), 10% HCl (2 L) and water (2 L). The material was dried over anhydrous MgSO4, filtered and solvent removed by rotavap to afford (103) as a clear, colourless oil (595 g, 64%).

Workup

  1. additionAfter the addition
  2. temperaturethe mixture refluxed for 2 hours
  3. temperatureAfter cooling to room temperature
  4. additionmixed well
  5. customseparated
  6. washThe organic phase was washed with water (2×2 L)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customsolvent removed by rotary evaporation
  10. additionthe material was poured into water (1 L)
  11. extractionextracted with chloroform (500 mL)
  12. customseparated
  13. washThe organic portion was washed with water (2 L), 10% HCl (2 L) and water (2 L)
  14. dry with materialThe material was dried over anhydrous MgSO4
  15. filtrationfiltered
  16. customsolvent removed by rotavap

Sources & evidence

ORD record
ord-4b59e48327ee44ec8a40e7334171e578
Source dataset
uspto-grants-2016_01
Patent number
US09227986B2

Reaction notes

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