Acetic Anhydride → 3-hydroxy-3-cyano-3,4-dihydro-2H-1,5-benzodioxepin

HRID 267766Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 267766
[C-:1]#[N:2].[K+].[O:4]=[C:5]1[CH2:11][O:10][C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[O:7][CH2:6]1.C(OC(=O)C)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>O>[OH:4][C:5]1([C:1]#[N:2])[CH2:6][O:7][C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[O:10][CH2:11]1

Komponenten

6

Edukt 4

HCID 7918Acetic AnhydrideHCID 9032Potassium CyanideHCID 10340Sodium CarbonateHCID 113097002H-1,5-Benzodioxepin-3(4H)-one

Produkt 1

HCID 155572933-hydroxy-3-cyano-3,4-dihydro-2H-1,5-benzodioxepin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 13.5 g. (208 millimoles) of potassium cyanide in 27 ml. of water is added dropwise to a mixture of 18.7 g. (114 millimoles) of 3-oxo-3,4-dihydro-2H-1,5-benzodioxepin and 21.2 g. (208 millimoles) of acetic anhydride with stirring and cooling. The mixture is stirred at ambient temperature overnight and then is made alkaline with 10% sodium carbonate solution. The product in the form of an oil is extracted with diethyl ether, treated with charcoal and dried over calcium sulfate. Evaporation of the solvent gives a solid that is recrystallized from carbon tetrachloride to give 3-hydroxy-3-cyano-3,4-dihydro-2H-1,5-benzodioxepin as plates, m.p. 108.5°-110° C.

Aufarbeitung

  1. temperaturecooling
  2. extractionThe product in the form of an oil is extracted with diethyl ether
  3. additiontreated with charcoal
  4. dry with materialdried over calcium sulfate
  5. customEvaporation of the solvent
  6. customgives a solid
  7. customthat is recrystallized from carbon tetrachloride

Quellen und Nachweise

ORD-Eintrag
ord-8fc40df85f644bf1842db4225c025993
Quelldatensatz
uspto-grants-1976_03
Patentnummer
US03944560

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