Sulfuric Acid → Cyclododecanone

HRID 1885075Notes

Reaction equation

HRID 1885075 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.C([O:17]N=O)(C)(C)C.ON1C(=O)C2=CC=CC=C2C1=O.S(=O)(=O)(O)O.[OH-].[Na+].C1(=NO)CCCCCCCCCCC1.[N+](C1CCCCCCCCCCC1)([O-])=O>C(O)(=O)C>[C:1]1(=[O:17])[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
80 °C

Procedure

Cyclododecane (1.66 g; 9.88 mmol), t-butylnitrite (2 mmol), N-hydroxyphthalimide (0.4 mmol), and acetic acid (2 ml) were placed in a flask and were stirred at 80° C. in an atmosphere of argon gas for 1 hour. The resulting mixture was further treated with sulfuric acid having a concentration of 98% by weight (50 mg) with stirring at 70° C. for 15 minutes. The reaction mixture was neutralized with sodium hydroxide and was analyzed to find that cyclododecanone oxime, nitrocyclododecane, and cyclododecanone were formed in yields of 39%, 7%, and 5%, respectively.

Workup

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

Sources & evidence

ORD record
ord-febf3c0d53bd4ab18809a4f851ef97bd
Source dataset
uspto-grants-2004_07
Patent number
US06768023B2

Reaction notes

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