Sulfuric Acid → Cyclododecanone

HRID 1885085Notes

Reaction equation

HRID 1885085 reaction equation
[CH2:1]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:13]N1C(=O)C2=CC=CC=C2C1=O.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:1]1(=[O:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

9

Reactant 7

HCID 1118Sulfuric AcidHCID 9268CyclododecaneHCID 10665N-HydroxyphthalimideHCID 10906Tert-Butyl nitriteHCID 14798Sodium HydroxideHCID 136762Cyclododecanone, oximeHCID 292842Nitrocyclododecane

Product 1

HCID 13246Cyclododecanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

Cyclododecane (3.32 g; 19.8 mmol), N-hydroxyphthalimide (0.8 mmol), and acetic acid (4 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 15 minutes with stirring at 70° C. in an atmosphere of argon gas for a total of 1.5 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 62%, 2%, and 5%, respectively.

Workup

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

Sources & evidence

ORD record
ord-92645d60d3ed4578876214263200d9e7
Source dataset
uspto-grants-2004_07
Patent number
US06768023B2

Reaction notes

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