1,6-Hexanediol → 1,6-Hexanediol, dimethanesulfonate

HRID 2279692Notes

Reaction equation

HRID 2279692 reaction equation
[CH2:1]([OH:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].[CH3:9][S:10](Cl)(=[O:12])=[O:11]>N1C=CC=CC=1>[CH3:9][S:10]([O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][O:8][S:10]([CH3:9])(=[O:12])=[O:11])(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 123741,6-HexanediolHCID 31297Methanesulfonyl chloride

Product 1

HCID 1457351,6-Hexanediol, dimethanesulfonateYield 32.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
5.5 °C

Procedure

A solution of 1,6-hexanediol (13.15 g, 111.3 mmol) in 70 mL of anhydrous pyridine was cooled to 0° C. using ice bath. To this methanesulfonyl chloride (27 g, 235.7 mmol) was slowly added under mixing such that the temperature was maintained at 5-6° C. The combined mixture was stirred overnight at the temperature below 10° C. and the precipitate formed was filtered off, washed with 20% HCl (3×), water (3×), 5% solution of sodium bicarbonate (3×), and then again with water (3×). Product was dried under vacuum to obtain Compound 1 as a white solid (yield 32.8%). The structure of Compound 1 is given below:

Workup

  1. additionunder mixing such that the temperature
  2. customthe precipitate formed
  3. filtrationwas filtered off
  4. washwashed with 20% HCl (3×), water (3×), 5% solution of sodium bicarbonate (3×)
  5. customProduct was dried under vacuum

Sources & evidence

ORD record
ord-4afbec9f17334b769cb0c3bed39013d0
Source dataset
uspto-grants-2015_09
Patent number
US09133343B2

Reaction notes

Loading…