4-Toluenesulfonyl chloride → 2-(2-Hydroxyethoxy)ethyl 4-methylbenzenesulfonate

HRID 2093240Notes

Reaction equation

HRID 2093240 reaction equation
[CH2:1]([OH:7])[CH2:2][O:3][CH2:4][CH2:5][OH:6].C(N(CC)CC)C.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>C(Cl)Cl.CO>[OH:7][CH2:1][CH2:2][O:3][CH2:4][CH2:5][O:6][S:21]([C:18]1[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=1)(=[O:23])=[O:22]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8117Diethylene GlycolHCID 8471Triethylamine

Product 1

HCID 112539712-(2-Hydroxyethoxy)ethyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of diethylene glycol (22 g, 207.5 mmol) in CH2Cl2 (100 ml) was added triethylamine (10.5 g, 103.75 mmol). 9.89 (51.8 mmol) Toluene-4-sulfonyl chloride was added in one portion. The solution was stirred at room temperature for 1 hour. TLC was performed in 5% MeOH in DCM. After ½ hour a TLC showed formation of product. After 1 hour and 15 minutes the reaction mixture was washed with 0.1 M KHSO3 and 5% NaHCO3. The organic phase was dried with Na2SO3 and evaporated under reduced pressure. The crude reaction mixture was trapped on silica and purified by flash chromatography on a CombiFlash companion instrument (330 g column) using Hexane/EtOAc 50/50. Structure confirmed NMR.

Workup

  1. waitAfter ½ hour a TLC showed
  2. waitAfter 1 hour
  3. wash15 minutes the reaction mixture was washed with 0.1 M KHSO3 and 5% NaHCO3
  4. dry with materialThe organic phase was dried with Na2SO3
  5. customevaporated under reduced pressure
  6. customThe crude reaction mixture
  7. custompurified by flash chromatography on a CombiFlash companion instrument (330 g column)

Sources & evidence

ORD record
ord-006bb60038aa4ec09cbf0e41df6d067b
Source dataset
uspto-grants-2013_05
Patent number
US08444955B2

Reaction notes

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