Réaction #50907

Équation de réaction

acetic acid ethyl

1-methoxy-4-vinyl naphthalene

acetylene dicarboxylic acid dimethyl ester

n-hexane

→

phenanthrene

Rendement 61.2%

Solvants

nitrobenzene

nitrobenzene

Conditions de réaction

Traitement

1. 1
   Autre200 ml, and they were reacted for 7 hours at the temperature of 130° C
2. 2
   TempératureAfter cooling
3. 3
   Autrewas obtained

Mode opératoire

1-methoxy-4-vinyl naphthalene 18.42 g (0.1 mol) and acetylene dicarboxylic acid dimethyl ester 28.42 g (0.2 mol) were dissolved in nitrobenzene, 200 ml, and they were reacted for 7 hours at the temperature of 130° C. After cooling, nitrobenzene was escaped in vapor under a reduced pressure condition, silica gel column chromatography (developing solvent n-hexane: an acetic acid ethyl=9:1) process was performed to residual elements, crude material, 23.08 g, was obtained. Further, objective phenanthrene compounds, 19.85 g (yield 61.2%) was obtained by recrystallizing from n-butanol. A melting point was 150.2 to 151.0° C. An infrared absorption spectrum of this phenanthrene compound is shown in FIG. 4.

Source