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

HRID 1250041Notes

Reaction equation

HRID 1250041 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.[CH:2]1([OH:1])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[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

6

Reactant 2

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

Product 3

HCID 924813-Oxabicyclo[10.1.0]tridecaneYield 49.5%HCID 13246CyclododecanoneYield 3.4%HCID 15595CyclododecanolYield 33.3%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Further, Neftekhimiya, 16(1), 119—119, (1976) discloses a method in which 1,2-epoxy-5,9-cyclododecadiene is brought into contact with hydrogen in the presence of a palladium-carrying catalyst under a hydrogen pressure of 9.06 MPa (80 atmospheres) at a temperature of 140° C. By this method, 49.5% of epoxycyclododecane, 33.3% of cyclododecanol and 3.4% of cyclododecanone were obtained. In this method, the yields of cyclododecanol and cyclododecanone were unsatisfactory.

Workup

  1. customat a temperature of 140° C

Sources & evidence

ORD record
ord-d9524469051d4f83992e747a163f0071
Source dataset
uspto-grants-2002_01
Patent number
US06335472B1

Reaction notes

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