3,7,11-Trimethyl-6-dodecen-1-yn-3-ol → 1,6-Dodecadien-3-ol, 3,7,11-trimethyl-

HRID 1977524Notes

Reaction equation

HRID 1977524 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:3]#[CH:4]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CCCCCC>[CH3:1][C:2]([OH:16])([CH2:5][CH2:6][CH:7]=[C:8]([CH3:15])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:13])[CH3:14])[CH:3]=[CH2:4]

Participants

4

Reactant 1

HCID 538357523,7,11-Trimethyl-6-dodecen-1-yn-3-ol

Product 1

HCID 1158391,6-Dodecadien-3-ol, 3,7,11-trimethyl-Yield 99.1%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 8058HexaneSolvent

Procedure

An autoclave having an internal volume of 3 liters was charged with 630 g of the 3,7,11-trimethyl-6-dodecen-1-yn-3-ol thus obtained, 270 g of hexane and 0.22 g of a Lindlar catalyst (supported on calcium carbonate) to carry out the hydrogenation for 4 hours under hydrogen pressure of 5 to 8 kg/cm2 (gauge pressure) at a temperature of 25 to 43° C. Thereafter, the catalyst was filtered off, and the resultant filtrate was concentrated with a rotary evaporator to give 630 g of crude 3,7,11-trimethyl-1,6-dodecadien-3-ol. Analysis by gas chromatography (column: DC-550, available from Gasukuro Kogyo Inc.; column length: 3 m; column temperature: 160° C.; and column: PEG-20M, available from Gasukuro Kogyo Inc.; column length: 3 m; column temperature: 190° C.) revealed that the conversion of 3,7,11-trimethyl-6-dodecen-1-yn-3-ol was 95.5%, and the selectivity to 3,7,11-trimethyl-1,6-dodecadien-3-ol was 94.6%.

Workup

  1. customthus obtained
  2. customfor 4 hours
  3. customat a temperature of 25 to 43° C
  4. filtrationThereafter, the catalyst was filtered off
  5. concentrationthe resultant filtrate was concentrated with a rotary evaporator

Sources & evidence

ORD record
ord-7488b75b18a5454cab7d737dabf5558c
Source dataset
uspto-grants-2001_05
Patent number
US06232506B1

Reaction notes

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