Dichlone → 1,4-Naphthalenedione, 2-chloro-3-[cis-4-(4-chlorophenyl)cyclohexyl]-

HRID 2061942Notes

Reaction equation

HRID 2061942 reaction equation
Cl[C:2]1[C:3](=[O:14])[C:4]2[C:9]([C:10](=[O:13])[C:11]=1[Cl:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C@H:22]2[CH2:27][CH2:26][C@H:25](C(O)=O)[CH2:24][CH2:23]2)=[CH:18][CH:17]=1.S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+]>C(#N)C.[N+]([O-])([O-])=O.[Ag+]>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]2[CH2:27][CH2:26][CH:25]([C:2]3[C:3](=[O:14])[C:4]4[C:9]([C:10](=[O:13])[C:11]=3[Cl:12])=[CH:8][CH:7]=[CH:6][CH:5]=4)[CH2:24][CH2:23]2)=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 8342DichloneHCID 62648Ammonium PersulfateHCID 178525693HCID 178525693, compound

Product 1

HCID 111010701,4-Naphthalenedione, 2-chloro-3-[cis-4-(4-chlorophenyl)cyclohexyl]-

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 6342AcetonitrileSolvent

Procedure

condensing 2,3-dichloro-1,4-naphthoquinone of formula (3) with trans 4-(4-chlorophenyl)cyclohexane-1-carboxylic acid of formula (4) in acetonitrile in presence of silver nitrate and ammonium persulfate in a suitable solvent to provide 2-[4-(4-chlorophenyl)cyclohexyl]-3-chloro-1,4-naphthoquinone of formula (5);

Sources & evidence

ORD record
ord-0b5fda4f64a24f20bb69f5c0a7e4aabd
Source dataset
uspto-grants-2012_10
Patent number
US08283499B2

Reaction notes

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