1,3-Benzodioxole → Catechol

HRID 37584

Reaktionsgleichung

Reaktionsgleichung von HRID 37584
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[O:3]C1.[CH2:10]([Li])[CH2:11][CH2:12][CH3:13]>CCCCCC.C(OCC)C.CCCCCC>[C:5]1([C:4](=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:3])[OH:1].[CH3:13][CH2:12][CH2:11][CH2:10][CH2:6][CH2:5][CH2:4][CH2:9][CH3:8]

Komponenten

6

Edukt 2

HCID 92291,3-BenzodioxoleHCID 178418339Butyllithium

Produkt 2

HCID 289CatecholHCID 8141Nonane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8058HexaneLösungsmittelHCID 21584099Diethylether hexaneLösungsmittel

Versuchsvorschrift

Cabiddu et al. describe in Journal of Organometallic Chemistry 136 139-146 (1977) two competitive reactions which occur by the treatment of 1,3-benzodioxole in hexane with n-butyllithium in diethyl ether/hexane at -10° C. After carbonation of the reaction mixture the authors detected the formation of 1,3-benzodioxole-4-carbonic acid, originated from the 4-lithium compound with a yield of 41% and in addition thereto pyrocatechol and n-nonane, as a result of cleavage of the ether bond with a yield of each 45% of theory.

Quellen und Nachweise

ORD-Eintrag
ord-42cb4256625243f2ab8083d5da57f827
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420301

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