Réaction #50909

Équation de réaction

p-t-butoxy styrene

acetylene dicarboxylic acid dimethyl ester

→

naphthalene

Rendement 142.9%

Solvants

nitrobenzene

Conditions de réaction

Traitement

1. 1
   Autre200 ml, and then reacted at the temperature of 140° C. for 5 hours
2. 2
   TempératureAfter cooling
3. 3
   Autrenitro benzene was removed under a reduced pressure, silica gel column chromatography (developing solvent n-hexane:acetic acid ethyl=9:1)
4. 4
   Autrethus 40.78 g crude material was obtained

Mode opératoire

p-t-butoxy styrene 35.25 g (0.2 mol) and acetylene dicarboxylic acid dimethyl ester 56.84 g (0.4 mol) were dissolved in nitrobenzene, 200 ml, and then reacted at the temperature of 140° C. for 5 hours. After cooling, nitro benzene was removed under a reduced pressure, silica gel column chromatography (developing solvent n-hexane:acetic acid ethyl=9:1) was performed to the residual, thus 40.78 g crude material was obtained. Further, 36.63 g (yield 57.9%) objective naphthalene compounds were obtained by recrystallizing through diisopropyl ether. Melt points were 82.0-83.0° C. This naphthalene compound's infrared absorption spectrum is indicated in FIG. 4.

Source