Acetone → (E)-Oct-3-en-2-one

HRID 464103Notes

Reaction equation

HRID 464103 reaction equation
[Li+].[I-].[CH3:3][C:4]([CH3:6])=[O:5].[CH:7](=O)[CH2:8][CH2:9][CH2:10][CH3:11].O>C(OCC)C>[CH3:3][C:4](=[O:5])/[CH:6]=[CH:7]/[CH2:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 8063PentanalHCID 66321Lithium iodide

Product 1

HCID 5363229(E)-Oct-3-en-2-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 7.73 g (58 mM) of anhydrous LiI and 1.47 ml (20 mM) of acetone in 35 ml of diethyl ether was heated to gentle reflux. To this solution was added dropwise a solution of 1.59 ml (15.0 mM) 1-pentanal in 5 ml diethyl ether over 10 minutes. The solution was then heated at reflux for 6 hours. After the solution was cooled to ambient temperature water was added and the layers separated. The ether phase was washed once with brine and dried over anhydrous MgSO4. The diethyl ether was removed by distillation at atmospheric pressure followed by distillation of the residue. There was obtained 0.52 g (27%) of a highly mobile colorless liquid. 1H NMR (CDCl3):6.80δ (dt,1H,JHH =7Hz, 16Hz), 6.01δ (d,1H,JHH =16Hz), 2.20δ (s,3H).

Workup

  1. temperatureThe solution was then heated
  2. temperatureat reflux for 6 hours
  3. additionwas added
  4. customthe layers separated
  5. washThe ether phase was washed once with brine
  6. dry with materialdried over anhydrous MgSO4
  7. customThe diethyl ether was removed by distillation at atmospheric pressure
  8. distillationfollowed by distillation of the residue
  9. customThere was obtained 0.52 g (27%) of a highly mobile colorless liquid

Sources & evidence

ORD record
ord-4ac4febf14dd4b0893b14d6cdc31cb0a
Source dataset
uspto-grants-1985_10
Patent number
US04546104

Reaction notes

Loading…