Ethylene Glycol → 1-Fluoro-3,7,11-trimethyldodeca-2,4,10-triene

HRID 918335Notes

Reaction equation

HRID 918335 reaction equation
Br[CH2:2][CH:3]=[C:4]([CH3:16])[CH:5]=[CH:6][CH2:7][CH:8]([CH3:15])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13].C(O)CO.[F-:21].[K+]>CCOCC>[F:21][CH2:2][CH:3]=[C:4]([CH3:16])[CH:5]=[CH:6][CH2:7][CH:8]([CH3:15])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 174Ethylene Glycol2×HCID 522689Potassium FluorideHCID 54370561HCID 54370561, compound

Product 1

HCID 538734921-Fluoro-3,7,11-trimethyldodeca-2,4,10-triene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 33 g. of 1-bromo-3,7,11-trimethyldodeca-2,4,10-triene and 100 ml. of dry ethylene glycol is slowly added with stirring, to a suspension of 11.5 g. of potassium fluoride in 30 ml. of dry ethylene glycol and heated to about 120°, under an inert atmosphere. When addition is completed, the reaction mixture is stirred for about an additional 16 hours while maintaining the temperature at 120°. Then the mixture is cooled and 200 ml. of ether added. The mixture is washed thoroughly with water and the ether phase dried over sodium sulfate and solvent evaporated under reduced pressure to yield 1-fluoro-3,7,11-trimethyldodeca-2,4,10-triene.

Workup

  1. additionA mixture of 33 g
  2. additionWhen addition
  3. stirringthe reaction mixture is stirred for about an additional 16 hours
  4. temperaturewhile maintaining the temperature at 120°
  5. temperatureThen the mixture is cooled
  6. washThe mixture is washed thoroughly with water
  7. dry with materialthe ether phase dried over sodium sulfate and solvent
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-0c27b4a3e06e4a76b667563f1bd9c9ca
Source dataset
uspto-grants-1976_07
Patent number
US03970704

Reaction notes

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