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ChemicalBook CAS DataBase List Oleyl Mesylate

Oleyl Mesylate synthesis

4synthesis methods
-

Yield:35709-09-2 90%

Reaction Conditions:

with sodium hydrogencarbonate in pyridine;ethanol;chloroform;water;methanesulfonyl chloride;

Steps:

1.a Step (a):

Step (a): Oleylmethanesulfonate In a 500 ml three-necked flask equipped with a dropping funnel, 5.0 g (18.7 mmoles) of oleyl alcohol (Nu Check Prep, Elysian, Minn. 56028) was dissolved in 6.67 ml of dry pyridine and 100 ml of freshly distilled chloroform. The solution was chilled in an ice bath and 3.22 g (28.14 mmoles) of methanesulfonyl chloride (Nu Check Prep) dissolved in 50 ml of dry chloroform was added dropwise during one hour. The reaction mixture was allowed to stir for another 4 hours at room temperature. At the end of the reaction period, 30 ml of ice cold water and 50 ml of diethylether was added. The organic layer was washed twice with 50 ml of 0.5N cold HCL, followed by 50 ml of cold 0.5N sodium bicarbonate. Finally, the organic phase was dried over anhydrous sodium sulfate and evaporated under vacuum on a rotary evaporator. The product was dissolved in 45 ml of absolute ethanol and crystallized at -20° C. Pure long needles of oleylmethanesulfonate were obtained in 90% yield.

References:

US5264618,1993,A