Methanol → 7-Methoxycycloheptatriene

HRID 745288Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 745288
[B-](F)(F)(F)F.[CH:6]1[CH:12]=[CH:11][CH+:10][CH:9]=[CH:8][CH:7]=1.CO.[C:15](=O)(O)[O-:16].[Na+]>O>[CH3:15][O:16][CH:6]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=[CH:7]1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 152926Cycloheptatrienylium, tetrafluoroborate(1-) (1:1)HCID 516892Sodium Bicarbonate

Produkt 1

HCID 1371707-Methoxycycloheptatriene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

1-methoxy-1,3,5-cycloheptatriene can be produced from cycloheptatrienyl tetrafluoroborate (I) as described in Conrow K 1963 Organic Synthesis 43, 101. The reaction of (I) with methanol and sodium bicarbonate in water gives 7-methoxy-1,3,5-cycloheptatriene (II), (reference Conrow K1961, J. Am. Chem. Soc. 83,2342). The 1-methoxy-1,3,5-cycloheptriene can be made by the thermal isomerisation of (II) by heating at 150° for 2.5 hours in nitrogen atmosphere in the presence of antioxidants and absence of water, as described by T. NOZOE and K., Takahashi, Bull Chem. Soc. Japan, 38, 665, 1965. Pratt, J. T. Reaction of Cycloheptatriene, PHD Thesis, University of Washington, Seattle, Wash. 1964.

Aufarbeitung

  1. customas described in Conrow K 1963 Organic Synthesis 43, 101

Quellen und Nachweise

ORD-Eintrag
ord-5a291a12543641bcadcb703bf3841894
Quelldatensatz
uspto-grants-1986_07
Patentnummer
US04598096

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