a Farnesol → (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienal

HRID 991269Notes

Reaction equation

HRID 991269 reaction equation
[OH:1][CH2:2][CH:3]=[C:4]([CH2:6][CH2:7][CH:8]=[C:9]([CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])[CH3:10])[CH3:5].C(OCC)(=O)C>CS(C)=O>[CH3:15][C:14]([CH3:16])=[CH:13][CH2:12][CH2:11]/[C:9](/[CH3:10])=[CH:8]/[CH2:7][CH2:6]/[C:4](/[CH3:5])=[CH:3]/[CH:2]=[O:1]

Participants

4

Reactant 2

HCID 3327a FarnesolHCID 8857Ethyl Acetate

Product 1

HCID 5280598(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienalYield 85%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5 g of the composition prepared in Example 7 are introduced in small fractions over a period of 15 minutes into a solution of 1.6 g of farnesol in 40 ml of dimethyl sulfoxide while maintaining the temperature at from 20° C. to 25° C. After 2 hours under agitation, the solution is poured into 100 ml of hexanes (petrol G) and the precipitate is separated off and washed with water and then with petrol G. The organic phases are concentrated under vacuum and the residue obtained is purified by chromatography over 25 g of R60 Merck® silica in order to separate the remaining stabilizing agent from the farnesal obtained; the eluent is petrol G and then its mixture with ethyl acetate (9/1-v/v). The pure farnesal is isolated with a yield of 85%.

Workup

  1. custom5 g of the composition prepared in Example 7
  2. temperaturewhile maintaining the temperature at from 20° C. to 25° C
  3. customthe precipitate is separated off
  4. washwashed with water
  5. concentrationThe organic phases are concentrated under vacuum
  6. customthe residue obtained
  7. customis purified by chromatography over 25 g of R60 Merck® silica in order
  8. customto separate the
  9. customobtained

Sources & evidence

ORD record
ord-807e24629de14dd5b5fe471da5e911d5
Source dataset
uspto-grants-2002_10
Patent number
US06462227B2

Reaction notes

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