Hydrochloric Acid → Diethylene glycol ditosylate

HRID 900516Notes

Reaction equation

HRID 900516 reaction equation
[CH2:1]([OH:7])[CH2:2][O:3][CH2:4][CH2:5][OH:6].[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.Cl>N1C=CC=CC=1>[S:14]([O:7][CH2:1][CH2:2][O:3][CH2:4][CH2:5][O:6][S:14]([C:11]1[CH:12]=[CH:13][C:8]([CH3:18])=[CH:9][CH:10]=1)(=[O:16])=[O:15])([C:11]1[CH:12]=[CH:13][C:8]([CH3:18])=[CH:9][CH:10]=1)(=[O:16])=[O:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8117Diethylene Glycol

Product 1

HCID 316659Diethylene glycol ditosylateYield 84.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 500 mL eggplant-shaped flask was charged with diethylene glycol 13 (15.0 mL, 155 mmol) and pyridine (300 mL), and p-toluenesulfonyl chloride (68.0 g, 351 mmol) was gradually added thereto in an ice bath. The mixture was stirred for 4 hours in the ice bath. Thereafter, a 1-L Erlenmeyer flask containing ice was charged with the reaction solution, and a concentrated hydrochloric acid (220 mL) was added thereto in the ice bath to adjust its pH to 4. The reaction mixture was subjected to suction filtration, and thereafter the residue was dissolved in chloroform. The mixture obtained was dried over anhydrous magnesium sulfate and concentrated, to give a product 12 (54.4 g, 131 mmol) in the form of a white solid (yield: 85%).

Workup

  1. additionwas gradually added
  2. additionThereafter, a 1-L Erlenmeyer flask containing ice
  3. additionwas charged with the reaction solution
  4. filtrationThe reaction mixture was subjected to suction filtration
  5. dissolutionthe residue was dissolved in chloroform
  6. customThe mixture obtained
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9a355be01dd14675bb1a3af69fb7af65
Source dataset
uspto-grants-2008_04
Patent number
US07358403B2

Reaction notes

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