4-Toluenesulfonyl chloride → Hexaethylene Glycol Di-p-toluenesulfonate

HRID 843513Notes

Reaction equation

HRID 843513 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:12]([OH:30])[CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][OH:29].C(N([CH2:36][CH3:37])CC)C>C(Cl)Cl>[S:7]([O:29][CH2:28][CH2:27][O:26][CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:30][S:7]([C:37]1[CH:36]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8])([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 17472Hexaethylene Glycol

Product 1

HCID 428918Hexaethylene Glycol Di-p-toluenesulfonateYield 103.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 73.91 g of p-toluenesulfonyl chloride (0.389 mol) in 400 mL of methylene chloride is added dropwise with stirring over a 2.5 hrs period to 400 mL of methylene chloride containing 50 g of hexaethylene glycol (0.177 mol) and 64 mL of triethylamine (39.36 g, 0.389 mol) at 0° C. The mixture is stirred for one hr at 0° C. and heated to ambient temperature for 44 hrs. The mixture is filtered and the filtrate concentrated in vacuo. The resulting residue is suspended in 500 mL of ethyl acetate and filtered. The filtrate is concentrated in vacuo to a yellow oil which was triturated eight times with 250 mL portions of warm hexane to remove unreacted p-toluenesulfonyl chloride. The resulting oil is then concentrated under high vacuum to yield 108.12 g of a yellow oil (quantitative yield).

Workup

  1. temperatureheated to ambient temperature for 44 hrs
  2. filtrationThe mixture is filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated in vacuo to a yellow oil which
  6. customwas triturated eight times with 250 mL portions of warm hexane
  7. customto remove unreacted p-toluenesulfonyl chloride
  8. concentrationThe resulting oil is then concentrated under high vacuum

Sources & evidence

ORD record
ord-83ef162efced4e1d8070af1baa12f198
Source dataset
uspto-grants-2002_04
Patent number
US06379930B1

Reaction notes

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