1,6-Dodecadien-3-ol, 3,7,11-trimethyl- → 5-Undecen-2-one, 6,10-dimethyl-

HRID 1977525Notes

Reaction equation

HRID 1977525 reaction equation
[CH3:1][C:2]([OH:16])([CH2:5][CH2:6][CH:7]=[C:8]([CH3:15])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])C=C.C[O-].[Na+].CC(O)(CCC=C(C)CCCC(C)C)C#C>>[CH3:15][C:8]([CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:7][CH2:6][CH2:5][C:2](=[O:16])[CH3:1]

Participants

4

Reactant 3

HCID 1158391,6-Dodecadien-3-ol, 3,7,11-trimethyl-HCID 10942334Sodium MethoxideHCID 538357523,7,11-Trimethyl-6-dodecen-1-yn-3-ol

Product 1

HCID 1018355-Undecen-2-one, 6,10-dimethyl-

Conditions

Temperature
150 °C

Procedure

To 630 g of the crude 3,7,11-trimethyl-1,6-dodecadien-3-ol thus obtained, 0.16 g of a methanolic sodium methoxide (concentration: 28%) was added, then the resulting mixture was heated at 150° C. for 1 hour to decompose unreacted 3,7,11-trimethyl-6-dodecen-1-yn-3-ol. Thereafter, the resultant solution was simple distilled under a pressure of 7 to 12 mmHg to collect 520 g of a fraction having a boiling point of 120 to 135° C. Analysis by gas chromatography (column: DC-550, available from Gasukuro Kogyo Inc.; column length: 3 m; column temperature: 160° C.) revealed that this fraction contained 93.7% of 3,7,11-trimethyl-1,6-dodecadien-3-ol (yield on the basis of 6,10-dimethyl-5-undecen-2-one: 78.0%).

Workup

  1. distillationThereafter, the resultant solution was simple distilled under a pressure of 7 to 12 mmHg
  2. customto collect 520 g of a fraction
  3. customby gas chromatography (column: DC-550, available from Gasukuro Kogyo Inc.; column length: 3 m; column temperature: 160° C.)

Sources & evidence

ORD record
ord-6a9e44e87e404522a0bbf579c340f132
Source dataset
uspto-grants-2001_05
Patent number
US06232506B1

Reaction notes

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