Reaktion #980432

Reaktionsgleichung

triphenylphosphine

(2S,5R)-hydroxy-5-hexyl-δ-valerolactone

p-octyloxybenzoic acid

azodicarboxylic acid

→

(2S,5R)-2-(4-octyloxybenzoyloxy)-5-hexyl-δ-valerolactone

Ausbeute 41.7%

Lösungsmittel

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigesynthesized in the same manner
2. 2
   workup.ADDITIONwas added to the dispersion and reaction
3. 3
   EinengenThe reacted solution was concentrated
4. 4
   Sonstigethe concentrate was separated
5. 5
   Sonstigepurified by the silica gel column chromatography
6. 6
   SonstigeThe obtained product was recrystallized from methanol

Vorschrift

In dehydrated benzene were dispersed 200 mg of (2S,5R)-hydroxy-5-hexyl-δ-valerolactone synthesized in the same manner as described in Referential Example 4, 250 mg of p-octyloxybenzoic acid and 200 μl of azodicarboxylic acid, and 270 mg of triphenylphosphine was added to the dispersion and reaction was carried out with stirring overnight. The reacted solution was concentrated, and the concentrate was separated and purified by the silica gel column chromatography using n-hexane/benzene as the developing solvent. The obtained product was recrystallized from methanol to obtain 180 mg of (2S,5R)-2-(4-octyloxybenzoyloxy)-5-hexyl-δ-valerolactone. The NMR spectrum of the obtained compound is shown in FIG. 1. The results of the measurement of the phase transition behavior by a differential thermal scanning calorimeter and a polarization microscope are shown below: ##STR23##

Quelle