Farnesol → (6E)-3,7,11-Trimethyl-6,10-dodecadien-1-ol

HRID 1088530Notes

Reaction equation

HRID 1088530 reaction equation
[CH3:1]/[C:2](/[CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:16])/[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])=[CH:3]\[CH2:4][OH:5].[H][H]>CO>[CH3:1][CH:2]([CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:16])/[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[CH2:3][CH2:4][OH:5]

Participants

4

Reactant 2

HCID 445070FarnesolHCID 178418361HCID 178418361, compound2×

Product 1

HCID 5280341(6E)-3,7,11-Trimethyl-6,10-dodecadien-1-olYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A nitrogen-purged 200-ml autoclave was charged with 22.1 g (0.1 mole) of (2E, 6E)-3,7,11-trimethyl2,6,10-dodecatrien-1-ol and 40 ml of methanol. To the solution, 4.8 mg (0.005 mmole) of the [Ru((-)-T-BINAP)](BF4)2 as prepared in Referential Example 6 was added, and hydrogenation was conducted at a hydrogen pressure of 30 kg/cm2 and at a reaction temperature of 20° C. for 10 hours. When it was confirmed that 0.1 mole of hydrogen had been absorbed, the solvent methanol was distilled off, and the residue was subjected to vacuum distillation to obtain 22 g of a (+)-(6E)-3,7,11- trimethyl-6,10-dodecadien-1-ol having a boiling point of 115 to 118° C./0.2 mmHg. The yield of this fraction was 99.5%.

Workup

  1. customA nitrogen-purged 200-ml autoclave
  2. additionwas added
  3. customhad been absorbed
  4. distillationthe solvent methanol was distilled off
  5. distillationthe residue was subjected to vacuum distillation

Sources & evidence

ORD record
ord-6d1c948b73a94b7d9038bb782f71ad37
Source dataset
uspto-grants-1990_10
Patent number
US04962242

Reaction notes

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