2-Chloro-1,4-naphthoquinone → HCID 20437477, compound

HRID 1980109Notes

Reaction equation

HRID 1980109 reaction equation
[Cl:1][C:2]1[C:3](=[O:13])[C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[C:14]([CH:18]1[CH2:23][CH2:22][CH:21](C(O)=O)[CH2:20][CH2:19]1)([CH3:17])(C)C.S1(CC[CH2:31][CH2:30]1)(=O)=O.S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+]>O.[N+]([O-])([O-])=O.[Ag+].C(#N)C>[CH2:14]([CH:18]1[CH2:19][CH2:20][CH:21]([C:11]2[C:10](=[O:12])[C:9]3[C:4]([C:3](=[O:13])[C:2]=2[Cl:1])=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:22][CH2:23]1)[CH2:17][CH2:30][CH3:31]

Participants

8

Reactant 4

HCID 138912-Chloro-1,4-naphthoquinoneHCID 31347SulfolaneHCID 62648Ammonium PersulfateHCID 1367594-Tert-butylcyclohexane-1-carboxylic acid

Product 1

HCID 20437477HCID 20437477, compound

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-chloro-1,4-naphthoquinone (21 g), 4-t-butylcyclohexane-1-carboxylic acid (19.8 g) and silver nitrate (3.6 g) was heated at 70°-75° C. with vigorous stirring in a solvent mixture of acetonitrile (30 ml), sulpholane (90 ml) and water (210 ml) whilst a solution of ammonium persulphate (34.2 g) in water (60 ml) was added dropwise during 30 minutes. Stirring and heating was continued for a further hour, the mixture cooled in ice and extracted with diethyl ether. The extracts were washed with aqueous sodium bicarbonate solution, dried and evaporated under reduced pressure to a semi-solid which was crystallised twice from acetonitrile to provide 2-(4-butylcyclohexyl)-3-chloro-1,4-naphthoquinone m.p. 107°-110°.

Workup

  1. temperaturewas heated at 70°-75° C.
  2. additionwas added dropwise during 30 minutes
  3. temperatureheating
  4. waitwas continued for a further hour
  5. temperaturethe mixture cooled in ice
  6. extractionextracted with diethyl ether
  7. washThe extracts were washed with aqueous sodium bicarbonate solution
  8. customdried
  9. customevaporated under reduced pressure to a semi-solid which
  10. customwas crystallised twice from acetonitrile

Sources & evidence

ORD record
ord-2b2ae6da62e74a5b968d7b2fdfc12c72
Source dataset
uspto-grants-1984_11
Patent number
US04485117

Reaction notes

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