Dimethyl acetylenedicarboxylate → Naphthalene

HRID 22631

Reaktionsgleichung

Reaktionsgleichung von HRID 22631
C(O[C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[CH2:11])=[CH:8][CH:7]=1)(C)(C)C.CO[C:16]([C:18]#CC(OC)=O)=O>[N+](C1C=CC=CC=1)([O-])=O>[CH:16]1[C:8]2[C:9](=[CH:12][CH:13]=[CH:6][CH:7]=2)[CH:10]=[CH:11][CH:18]=1

Komponenten

4

Edukt 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 5775311-(Tert-butoxy)-4-ethenylbenzene

Produkt 1

HCID 931NaphthaleneAusbeute 142,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7416NitrobenzeneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. custom200 ml, and then reacted at the temperature of 140° C. for 5 hours
  2. temperatureAfter cooling
  3. customnitro benzene was removed under a reduced pressure, silica gel column chromatography (developing solvent n-hexane:acetic acid ethyl=9:1)
  4. customthus 40.78 g crude material was obtained

Quellen und Nachweise

ORD-Eintrag
ord-72041597c8174feb98f00887889851c6
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849367B2

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