Réaction #5717

Équation de réaction

methyl (R)-3-hydroxytetradecanoate

benzyl trichloroacetimidate

trifluoromethanesulphonic acid

→

methyl (R)-3-(benzyloxy)-tetradecanoate

Rendement 112.8%

Solvants

cyclohexane

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas treated under nitrogen
2. 2
   workup.DISSOLUTIONdissolved at 20°
3. 3
   Températurewhile cooling in an ice/water bath in such a manner that the temperature
4. 4
   Autreremains between 20°-23°
5. 5
   FiltrationThe precipitate was filtered off
6. 6
   Lavagethe filter cake was washed with cyclohexane
7. 7
   Extractionthe filtrates were extracted with sat. NaHCO3 solution, water and sat. NaCl solution
8. 8
   SéchageThe organic phase was dried over magnesium sulphate
9. 9
   Filtrationfiltered
10. 10
    Lavagethe filter cake was washed with cyclohexane
11. 11
    Autrethe filtrates were evaporated

Mode opératoire

A suspension of 206.7 g of methyl (R)-3-hydroxytetradecanoate in 1000 ml of cyclohexane was treated under nitrogen and while stirring with 214.2 g of benzyl trichloroacetimidate and dissolved at 20°. 10 ml of trifluoromethanesulphonic acid were added dropwise while cooling in an ice/water bath in such a manner that the temperature remains between 20°-23°. The resulting suspension was stirred at 25°-30°. The precipitate was filtered off, the filter cake was washed with cyclohexane, the filtrates were extracted with sat. NaHCO3 solution, water and sat. NaCl solution. The organic phase was dried over magnesium sulphate, filtered, the filter cake was washed with cyclohexane and the filtrates were evaporated. 314.5 g of methyl (R)-3-(benzyloxy)-tetradecanoate were obtained.

Source