Sulfuric Acid → Cyclododecanone

HRID 1885088Notes

Reaction equation

HRID 1885088 reaction equation
C1CCCCCCCCCCC1.[CH2:13]([O:25]C(C1C=C2C(=O)N(O)C(=O)C2=CC=1)=O)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].N(OC(C)(C)C)=O.S(=O)(=O)(O)O.[OH-].[Na+].C1(=NO)CCCCCCCCCCC1.[N+](C1CCCCCCCCCCC1)([O-])=O>C(O)(=O)C>[C:13]1(=[O:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]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 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

Cyclododecane (3.32 g; 19.8 mmol), 4-lauryloxycarbonyl-N-hydroxyphthalimide (0.8 mmol), and acetic acid (1 ml) were placed in a flask, t-butyl nitrite (4 mmol) was added to the mixture in four installments of 1 mmol each once every 30 minutes with stirring at 70° C. in an atmosphere of argon gas for a total of 2.5 hours. The resulting mixture 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 41%, 6%, and 4%, respectively.

Workup

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

Sources & evidence

ORD record
ord-709f16dc743a42278a7f4831816c65e5
Source dataset
uspto-grants-2004_07
Patent number
US06768023B2

Reaction notes

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