Sulfuric Acid → Cyclododecanone

HRID 1885089Notes

Reaction equation

HRID 1885089 reaction equation
C1CCCCCCCCCCC1.N(OC(C)(C)C)=O.[CH2:20]([O:32]C(C1C=C2C(=O)N(O)C(=O)C2=CC=1)=O)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].S(=O)(=O)(O)O.[OH-].[Na+].C1(=NO)CCCCCCCCCCC1.[N+](C1CCCCCCCCCCC1)([O-])=O>CCOCC>[C:20]1(=[O:32])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1

Participants

9

Reactant 7

HCID 1118Sulfuric AcidHCID 9268CyclododecaneHCID 10906Tert-Butyl nitriteHCID 14798Sodium HydroxideHCID 136762Cyclododecanone, oximeHCID 292842NitrocyclododecaneHCID 109157654-dodecyloxycarbonyl-N-hydroxyphthalimide

Product 1

HCID 13246Cyclododecanone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
70 °C

Procedure

Cyclododecane (3.32 g; 19.8 mmol), t-butyl nitrite (1 mmol), and 4-lauryloxycarbonyl-N-hydroxyphthalimide (0.5 mmol) were placed in a flask and were stirred at 70° C. in an atmosphere of argon gas for 2 hours. The resulting mixture was diluted with ether (2 ml) and was further treated with sulfuric acid having a concentration of 98% by weight (200 mg) with stirring at 70° C. for 15 minutes. The reaction mixture was then neutralized with sodium hydroxide and was analyzed to find that cyclododecanone oxime, nitrocyclododecane, and cyclododecanone were formed in yields of 58%, 5%, and 3%, respectively.

Workup

  1. stirringwith stirring at 70° C. for 15 minutes

Sources & evidence

ORD record
ord-1bb933cc793049abb2d481c45deabbd0
Source dataset
uspto-grants-2004_07
Patent number
US06768023B2

Reaction notes

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