Selenium Dioxide → 2-Fluorenonylglyoxal
Reaction equation
[C:1]([C:4]1[C:5](=[O:17])[C:6]2[C:14](=[CH:15][CH:16]=1)[C:13]1[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH:7]=2)(=[O:3])[CH3:2].[Se](=O)=[O:19]>O1CCOCC1>[C:5]1(=[O:17])[C:6]2[C:14]([C:13]3[C:8]([CH:7]=2)=[CH:9][CH:10]=[CH:11][CH:12]=3)=[CH:15][CH:16]=[C:4]1[C:1](=[O:3])[CH:2]=[O:19]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The thus-isolated 2-acetylfluorenon is oxidized by selenium dioxide in dioxane medium at 98°-100° C during 22 hours to obtain 2-fluorenonyl-glyoxal isolated as semiacetal, the yield being equal to 31.2 weight percent. The thus-obtained intermediate product is subjected to treatment with sodium bisulfite in 60-percent ethanol to obtain the final product crystallizable with a molecule of water. The yield of the final product amounts to 57 weight percent when calculated for the semiacetal of 2-fluorenonyl-glyoxal and to 55 weight percent when calculated for the parent fluorene (of.Sintez organicheskikh preparatov/synthesis of organic preparations/, v.4, P.77, 1953 /in Russian/; Zhurnal organicheskoy khimii /Journal of organic chemistry/, 33, 3053, 1963 (in Russian).
Sources & evidence
- ORD record
- ord-19b7dec615684202a30dc56823abd3cc
- Source dataset
- uspto-grants-1977_04
- Patent number
- US04016289
Reaction notes
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