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

HRID 2226357Notes

Reaction equation

HRID 2226357 reaction equation
[CH2:1]([OH:19])[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][OH:18].C(N([CH2:25][CH3:26])CC)C.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>C(Cl)Cl>[S:33]([O:18][CH2:17][CH2:16][O:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][O:3][CH2:2][CH2:1][O:19][S:33]([C:26]1[CH:25]=[CH:32][C:27]([CH3:37])=[CH:28][CH:29]=1)(=[O:35])=[O:34])([C:30]1[CH:31]=[CH:32][C:27]([CH3:37])=[CH:28][CH:29]=1)(=[O:35])=[O:34]

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

To a stirred solution containing 50 g of hexaethylene glycol (0.177 mol) and 64 ml of triethylamine (39.36 g, 0.389 mol) in 400 ml of CH2Cl2 at 0° C. was added dropwise a solution containing 73.91 g of p-toluenesulfonyl chloride (0.389 mol) in 400 ml of CH2Cl2 over a 2.5 hour period. The reaction mixture was then stirred for one hour at 0° C. and then heated to ambient temperature for 44 hours. The mixture was then filtered and the filtrate was concentrated in vacuo. The resulting heterogeneous residue was suspended in 500 ml of ethyl acetate and filtered. The filtrate was then 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 was then concentrated under high vacuum to yield 108.12 g of a yellow oil (quantitative yield).

Workup

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

Sources & evidence

ORD record
ord-78ac6095f5ff4d8eb8294927893b10aa
Source dataset
uspto-grants-1994_09
Patent number
US05348855

Reaction notes

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