Hydrochloric Acid → 6-Methanesulfonyloxyundecane

HRID 23800Notes

Reaction equation

HRID 23800 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([OH:12])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[CH3:13][S:14](Cl)(=[O:16])=[O:15].Cl>N1C=CC=CC=1>[CH3:13][S:14]([O:12][CH:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])(=[O:16])=[O:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 320456-Undecanol

Product 1

HCID 225905206-MethanesulfonyloxyundecaneYield 105%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

After dissolving 29.95 g (0.17 mol) of 6-undecanol to 60 mL of pyridine, 29.98 g (0.26 mol) of methanesulfonyl chloride was added dropwise under cooling with ice and the mixture was stirred overnight. Thereafter, 35 mL of 0.5 N aqueous hydrochloric acid was added and the mixture was extracted twice with 200 mL of ethyl acetate. The organic layer was washed with 100 mL of water and a saturated aqueous solution of sodium chloride in that order and thereafter dried over anhydrous magnesium sulfate. After filtering off the magnesium sulfate, the solvent was distilled off to give 44.7 g of 6-methanesulfonyloxy-undecane.

Workup

  1. additionwas added dropwise
  2. temperatureunder cooling with ice
  3. extractionthe mixture was extracted twice with 200 mL of ethyl acetate
  4. washThe organic layer was washed with 100 mL of water
  5. dry with materiala saturated aqueous solution of sodium chloride in that order and thereafter dried over anhydrous magnesium sulfate
  6. filtrationAfter filtering off the magnesium sulfate
  7. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-3b7346425a634f4ba57e2850799830cb
Source dataset
uspto-grants-2005_02
Patent number
US06852867B2

Reaction notes

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