13-Oxabicyclo[10.1.0]tridecane → Cyclododecanone
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.[Li+].[Br-]>>[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]1Participants
Procedure
Soviet Union (SU) Patent No. 407,874 discloses an isomerization reaction of an epoxycyclododecane compound in the presence of anhydrous LiBr without using a solvent. In examples disclosed in the SU patent, it is reported that when the isomerization was carried out at a reaction temperature of 120 to 130° C. for 18 hours or at a temperature of 200° C. for 3 hours, the target cyclododecanone was obtained in a yield of about 100% in the former or 83.3% in the latter. In the former case, the reaction time was too long and thus the reaction conditions may not be practical. Also, in the latter case, a by-product having a high boiling temperature was produced and a discoloration of the reaction liquid was found. When the catalyst is recycled and repeatedly used, the high boiling temperature product accumulated in the reaction system causes the reaction to be affected and a specific procedure for removing the high boiling temperature product to be necessary.
Sources & evidence
- ORD record
- ord-04fad41f74db41b18e44945cacd72951
- Source dataset
- uspto-grants-2002_05
- Patent number
- US06388140B2
Reaction notes
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