Ethanol → Linoleyl methanesulfonate

Participants

Reaction Conditions

Reaction Steps

Dehydrated toluene (500 g), linoleyl alcohol (cis,cis-9,12-octadecadiene-1-ol, 100 g, 375 mmol), and triethylamine (46 g, 450 mmol) were added to a four-necked flask, and agitation was performed in a nitrogen atmosphere. After cooling to 10° C., methanesulfonyl chloride (47 g, 413 mmol) was dropped over 2 hours in such a way that the reaction temperature became 30° C. or lower. One hour from completion of dropping, the reaction solution was sampled, and disappearance of a spot of linoleyl alcohol was ascertained through TLC (chloroform development, phosphoric acid-copper sulfate color development). Ethanol (5.2 g, 113 mmol) was added, and triethylamine hydrochloric acid salts were filtrated. The filtrate was washed with ion-exchanged water (150 g), and the water layer was discarded. The same operation of washing with ion-exchanged water was performed again. The organic layer was dehydrated with anhydrous magnesium sulfate (20 g) and, thereafter, filtration and concentration were performed, so as to obtain linoleyl methane sulfonate (amount of production: 120 g, yield: 93%).

Provenance & Evidence