13-Oxabicyclo[10.1.0]tridecane → Cyclododecanone

HRID 982919Notes

Reaction equation

HRID 982919 reaction equation
[O:1]1[CH:3]2[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:2]12>CN1CCCC1=O.CN1C(=O)N(C)CC1.[Cl-].[Li+]>[C:2]1(=[O:1])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 1

HCID 924813-Oxabicyclo[10.1.0]tridecane

Product 1

HCID 13246CyclododecanoneYield 94%

Reagents, catalysts & solvents 3

HCID 433294Lithium ChlorideCatalystHCID 66611,3-Dimethyl-2-imidazolidinoneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

For example, German Patent DE3744094 discloses a technique where an epoxycyclododecane is isomerized by using N-methylpyrrolidone or N,N′-dimethylethyleneurea as a solvent and using lithium chloride as a catalyst and thereby a cyclododecanone is obtained in a yield of 94%.

Sources & evidence

ORD record
ord-1fb537af28774adc941b5f3d5d94fdeb
Source dataset
uspto-grants-2005_03
Patent number
US06861563B2

Reaction notes

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