13-Oxabicyclo[10.1.0]tridecane → Cyclododecanone

HRID 2228882Notes

Reaction equation

HRID 2228882 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.[I-].[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

3

Reactant 2

HCID 924813-Oxabicyclo[10.1.0]tridecaneHCID 66321Lithium iodide

Product 1

HCID 13246CyclododecanoneYield 91.2%

Procedure

Further, Zh. Org. Khim (1990), 26(7), 1497-1500, discloses that when an isomerization reaction of an epoxycyclododecane was carried out in the presence of 2.3 molar % of a catalyst consisting of LiBr (lithium bromide) at a reaction temperature of 150° C. for a reaction time of 10 hours, the target cyclododecanone was obtained at a yield of 96.6%, and when the reaction of the epoxycyclododecane was effected in the presence of 1.5 molar % of LiI (lithium iodide) at 150° C. for 5 hours, the target cyclododecanone was obtained at a yield of 91.2%. In the case of this report, however, it is assumed that to make the conversion of the epoxycyclododecane close to 100%, a very long reaction time is necessary. Also, the reaction of the report was effected in a batch-type reaction system, and thus no continuous method for the reaction is disclosed in the report.

Workup

  1. customat 150° C.
  2. customfor 5 hours

Sources & evidence

ORD record
ord-afc397386edf4ef6a4ec69bc8b8698db
Source dataset
uspto-grants-2002_07
Patent number
US06417404B1

Reaction notes

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