1,3-Benzodioxole → Catechol

반응식

[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]

참가 물질

실험 절차

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.