4-[(2-Methylbut-3-yn-2-yl)oxy]benzonitrile → 2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

HRID 1074411

Reaktionsgleichung

Reaktionsgleichung von HRID 1074411
[C:1]([C:3]1[CH:14]=[CH:13][C:6]([O:7][C:8]([CH3:12])([CH3:11])[C:9]#[CH:10])=[CH:5][CH:4]=1)#[N:2]>CCN(C1C=CC=CC=1)CC>[CH3:12][C:8]1([CH3:11])[O:7][C:6]2[CH:13]=[CH:14][C:3]([C:1]#[N:2])=[CH:4][C:5]=2[CH:10]=[CH:9]1

Komponenten

3

Edukt 1

HCID 27790724-[(2-Methylbut-3-yn-2-yl)oxy]benzonitrile

Produkt 1

HCID 27790742,2-dimethyl-2H-1-benzopyran-6-carbonitrileAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7061N,N-DiethylanilineLösungsmittel

Versuchsvorschrift

Cyclisation of the 3-(p-cyanophenoxy)-3-methybut-1-yne (9.77 g) was accomplished by heating in diethylaniline at 210°-220° C. under nitrogen. Purification by distillation, and extraction with dilute hydrochloric acid gave 2,2-dimethyl-6-cyano-2H-benzo[b]pyran as a colourless oil (6.84 g), which slowly crystallised on standing, having a nmr spectrum showing signals at δ146, 6.25 (d, J=10), 5.67 (d, J=10), 6.74 (d, J=8), 7.18 (d, J=2), 7.34 (q, J=8,2).

Aufarbeitung

  1. customPurification
  2. distillationby distillation, and extraction with dilute hydrochloric acid

Quellen und Nachweise

ORD-Eintrag
ord-06eb7d48bcf445648835b26d68e288c3
Quelldatensatz
uspto-grants-1983_07
Patentnummer
US04391815

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