Hydrochloric Acid → 1-Butyryl-1-(4-chlorophenyl)cyclobutane

HRID 35699

Reaktionsgleichung

Reaktionsgleichung von HRID 35699
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]#N)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl[C:15]1C=C(C2(C#N)CCC2)C=[CH:19][C:20]=1Cl.[Mg].C(Br)CC.Cl.CC[O:36]CC>O1CCCC1>[C:12]([C:8]1([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:11][CH2:10][CH2:9]1)(=[O:36])[CH2:15][CH2:20][CH3:19]

Komponenten

8

Edukt 6

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether3×HCID 78401-BromopropaneHCID 986211-(4-Chlorophenyl)cyclobutanecarbonitrileHCID 5462224MagnesiumHCID 108571341-(3,4-Dichlorophenyl)-1-cyclobutane-carbonitrile

Produkt 1

HCID 130833671-Butyryl-1-(4-chlorophenyl)cyclobutane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1-(4-Chlorophenyl)-1-cyclobutanecarbonitrile (15 g) prepared in a similar manner to the 1-(3,4-dichlorophenyl)cyclobutanecarbonitrile of Example 1 in dry ether (50 ml) was added to the product of the reaction between magnesium turnings (3.18 g) and propyl bromide (15.99 g) in dry ether (50 ml). The ether was replaced by tetrahydrofuran and the mixture heated with stirring under reflux for eighteen hours. The mixture was cooled and ice and then concentrated hydrochloric acid (52 ml) added. The resulting mixture was stirred under reflux for ten hours and extracted with ether. The ether extract yielded a residue from which 1-butyryl-1-(4-chlorophenyl)cyclobutane (b.p. 106°-108°/0.3 mm Hg) was distilled.

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureunder reflux for eighteen hours
  3. temperatureThe mixture was cooled
  4. stirringThe resulting mixture was stirred
  5. temperatureunder reflux for ten hours
  6. extractionextracted with ether
  7. extractionThe ether extract

Quellen und Nachweise

ORD-Eintrag
ord-6f8933fba88e466eb7e9c768e979dc7a
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04767790

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