Reaktion #323673

Reaktionsgleichung

tert-butyl 3-hexadecanoyloxyoctadecanoate

→

3-hexadecanoyloxyoctadecanoic acid

Ausbeute 108.0%

Lösungsmittel

trifluoroacetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTrifluoroacetic acid was removed off under reduced pressure
2. 2
   workup.ADDITIONto the residue was added dry benzene
3. 3
   Sonstigefollowed by evaporation of the solvent
4. 4
   workup.ADDITIONTo a solution of the dried residue in ethyl acetate (250 ml) were added N-hydroxysuccinimide (3.21 g) and N,N'-dicyclohexylcarbodiimide (5.75 g)
5. 5
   workup.STIRRINGThe mixture was stirred at ambient temperature overnight
6. 6
   Filtrationfiltered
7. 7
   Sonstigeto remove N,N'-dicyclohexylurea
8. 8
   Sonstigecondensed
9. 9
   Sonstigedried up by high vacuum pump

Vorschrift

To tert-butyl 3-hexadecanoyloxyoctadecanoate (16.56 g) was added trifluoroacetic acid (20 ml) and the mixture was stirred at room temperature for 1 hour. Trifluoroacetic acid was removed off under reduced pressure, and to the residue was added dry benzene, followed by evaporation of the solvent. This operation was repeated three times. To a solution of the dried residue in ethyl acetate (250 ml) were added N-hydroxysuccinimide (3.21 g) and N,N'-dicyclohexylcarbodiimide (5.75 g). The mixture was stirred at ambient temperature overnight and then filtered to remove N,N'-dicyclohexylurea. The filtrate was condensed and dried up by high vacuum pump to give N-hydroxysuccinimide ester of 3-hexadecanoyloxyoctadecanoic acid (16.2 g).

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