1,2-Epoxycyclododeca-5,9-diene → 13-Oxabicyclo[10.1.0]tridecane

HRID 1058207Notes

Reaction equation

HRID 1058207 reaction equation
[O:1]1[CH:3]2[CH2:4][CH2:5][CH:6]=[CH:7][CH2:8][CH2:9][CH:10]=[CH:11][CH2:12][CH2:13][CH:2]12.[H][H]>[Pd]>[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

Participants

4

Reactant 2

HCID 791351,2-Epoxycyclododeca-5,9-dieneHCID 178418361HCID 178418361, compound

Product 1

HCID 924813-Oxabicyclo[10.1.0]tridecane

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

As a process for producing cyclododecanone and cyclododecanol by a catalytic reaction of epoxycyclododecane compounds with hydrogen, J. Mol. Catal., Vol 169, pp 95-103 (1991) discloses a catalytic hydrogenating reaction of 2-epoxy-5,9-cyclododecadiene with hydrogen. In this reaction of the reference, 1,2-epoxy-5,9-cyclododecadiene is brought into contact with hydrogen in the presence of a palladium-carrying catalyst at a reaction temperature of 90° C. under a hydrogen gas pressure of 1,275 kPa (13 kg/cm2) on gauge, and epoxycyclododecane is produced as a principal reaction product. Cyclododecanol is produced as a by-product in a yield of 4% and no cyclododecanone is produced. Also, the Draft of 24-th Symposium “Development of Reaction and Synthesis, Nov. 5-6, 1998, pp 68, discloses a process of catalytic reaction of 1,2-epoxy-5,9-cyclododecadiene with hydrogen in the presence of a palladium catalyst at room temperature under the ambient atmospheric pressure. In this process, epoxycyclododecane is produced as a principal product, cyclododecanol is produced, as a by-product, in a yield of 5%, and no cyclododecanone is produced.

Workup

  1. customAlso, the Draft of 24-th Symposium “Development of Reaction and Synthesis, Nov

Sources & evidence

ORD record
ord-955891e8821f492a87c22b88d4bfbc19
Source dataset
uspto-grants-2003_02
Patent number
US06515185B1

Reaction notes

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