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

HRID 1065992Notes

Reaction equation

HRID 1065992 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 niL of methylene chloride containing 50 g of hexaethylene glycol (0.177 mol) and 64 miL 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-57e34a50c4534aafb3f668956a30d361
Source dataset
uspto-grants-2001_06
Patent number
US06242188B1

Reaction notes

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