Ethanol → 3,3-Diethoxy-2-fluorohex-1-ene

HRID 1995452Notes

Reaction equation

HRID 1995452 reaction equation
[CH2:1]([C:5]1([O:10][CH2:11][CH3:12])[CH2:7][C:6]1(Cl)[F:8])[CH2:2][CH2:3]C.C(=O)([O-])[O-].[K+].[K+].[CH2:19]([OH:21])[CH3:20]>>[CH2:19]([O:21][C:5]([O:10][CH2:11][CH3:12])([CH2:1][CH2:2][CH3:3])[C:6]([F:8])=[CH2:7])[CH3:20]

Participants

4

Reactant 3

HCID 702EthanolHCID 11430Potassium CarbonateHCID 127862351-Butyl-2-chloro-1-ethoxy-2-fluorocyclopropane

Product 1

HCID 127862363,3-Diethoxy-2-fluorohex-1-ene

Procedure

A stirred solution of 58.4 g. of 2-butyl-1-chloro-2-ethoxy-1-fluorocyclopropane and 166 g. of anhydrous potassium carbonate in 400 ml. of absolute ethanol is heated at reflux for 18 hours. The solution is cooled and the bulk of the ethanol is removed in vacuo. The residue is partitioned with 500 ml. of water and 750 ml. of ether. The ether phase is washed with three 100 ml. portions of brine, dried over potassium carbonate and concentrated in vacuo to provide 54 g. of a pale yellow oil. A 4.45 g. portion of this oil is distilled through a 6 inch Vigreux column giving 2.5 g. of the desired product as a colorless liquid, b.p. 80°-81° C., 24 mm.

Workup

  1. temperatureat reflux for 18 hours
  2. temperatureThe solution is cooled
  3. customthe bulk of the ethanol is removed in vacuo
  4. customThe residue is partitioned with 500 ml
  5. washThe ether phase is washed with three 100 ml
  6. dry with materialportions of brine, dried over potassium carbonate
  7. concentrationconcentrated in vacuo
  8. customto provide 54 g
  9. distillationportion of this oil is distilled through a 6 inch Vigreux column
  10. customgiving 2.5 g

Sources & evidence

ORD record
ord-77bb0643e9c0493496548177d630b413
Source dataset
uspto-grants-1983_09
Patent number
US04404393

Reaction notes

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