Реакция #1132517

Уравнение реакции

3-allyloxypropane-1,2-diol

linoleyl mesylate

sodium hydroxide

→

1,2-Dilinoleyloxy-3-allyloxypropane

Растворители

toluene

Условия реакции

Обработка

1. 1
   ДругоеIn a 2000 mL round bottom flask equipped with a large magnetic stir bar
2. 2
   workup.ADDITIONadded
3. 3
   Промывкаrinsing in with deionized water (20 mL)
4. 4
   workup.ADDITIONDeionized water (200 mL) and isopropyl acetate (200 mL) were added
5. 5
   workup.STIRRINGthe mixture stirred vigorously for a further 10-15 min
6. 6
   Другоеseparating funnel
7. 7
   Другоеto separate
8. 8
   ДругоеThe aqueous phase was removed
9. 9
   Промывкаthe organic phase washed with saturated sodium chloride solution (2×150 mL)
10. 10
    СушкаThe organic phase was dried with magnesium sulfate (40 g)
11. 11
    Фильтрацияfiltered
12. 12
    Концентрированиеconcentrated
13. 13
    Другоеto obtain a neat orange oil
14. 14
    ДругоеThe oil was purified by column chromatography

Методика

In a 2000 mL round bottom flask equipped with a large magnetic stir bar, 3-allyloxypropane-1,2-diol (5.94 g, 45 mmol), and tetrabutylammonium hydrogen sulfate (6 g, 18 mmol) were added. A solution of linoleyl mesylate (33.8 g, 98 mmol) in toluene (150 mL) was also made and added. The mixture was cooled to 0-5° C. with an ice bath. 50% sodium hydroxide (70 mL) was then slowly added, rinsing in with deionized water (20 mL). The resulting mixture is stirred at room temperature, under nitrogen for 40 hours. Deionized water (200 mL) and isopropyl acetate (200 mL) were added and the mixture stirred vigorously for a further 10-15 min. The mixture was transferred to a 1000-mL separating funnel and allowed to separate. The aqueous phase was removed and the organic phase washed with saturated sodium chloride solution (2×150 mL). The organic phase was dried with magnesium sulfate (40 g), filtered, and concentrated to obtain a neat orange oil. The oil was purified by column chromatography. Final yield: 19.5 g (69%).

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