Hydrochloric Acid → HCID 86595492, compound

HRID 1774139Notes

Reaction equation

HRID 1774139 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]([CH2:8][CH2:9][OH:10])[CH2:5][CH2:6][OH:7].[CH3:11][S:12](Cl)(=[O:14])=[O:13].N1C=CC=CC=1.Cl>ClCCl>[CH3:11][S:12]([O:1][CH2:2][CH2:3][CH:4]([CH2:8][CH2:9][O:10][S:12]([CH3:11])(=[O:14])=[O:13])[CH2:5][CH2:6][O:7][S:12]([CH3:11])(=[O:14])=[O:13])(=[O:14])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 12053840tris(2hydroxyethyl)methane

Product 1

HCID 86595492HCID 86595492, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To an stirred ice-cooled solution of tris(2-hydroxyethyl)methane (10 g, 0.0676 mol) in dichloromethane (50 ml) was slowly dripped a solution of methanesulfonyl chloride (40 g, 0.349 mol) in dichloromethane (50 ml) under nitrogen at such a rate that the temperature did not rise above 15° C. Pyridine (21.4 g, 0.27 mol, 4 eq) dissolved in dichloromethane (50 ml) was then added drop-wise at such a rate that the temperature did not rise above 15° C., exothermic reaction. The reaction was left to stir at room temperature for 24 h and then treated with 5N hydrochloric acid solution (80 ml) and the layers separated. The aqueous layer was extracted with further dichloromethane (50 ml) and the organic extracts combined, dried over sodium sulfate, filtered and concentrated in vacuo to give tris[2-(methylsulfonyloxy)ethyl]methane contaminated with excess methanesulfonyl chloride. The theoretical yield was 25.8 g.

Workup

  1. customdid not rise above 15° C
  2. additionwas then added drop-wise at such a rate that the temperature
  3. customdid not rise above 15° C.
  4. customexothermic reaction
  5. waitThe reaction was left
  6. customthe layers separated
  7. extractionThe aqueous layer was extracted with further dichloromethane (50 ml)
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-20f8d518ab3d43ca8c2b5ee3c9e4c94f
Source dataset
uspto-grants-2016_02
Patent number
US09259496B2

Reaction notes

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