Hydrochloric Acid → 6-Methanesulfonyloxyundecane

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

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.