Hydrochloric Acid → HCID 19809727, compound

HRID 374326Notes

Reaction equation

HRID 374326 reaction equation
[CH3:1]I.[CH3:3][C:4]1([CH3:11])[CH2:8][C:7]([CH:9]=[O:10])=[CH:6][CH2:5]1.Cl>CI.C(OCC)C>[CH3:3][C:4]1([CH3:11])[CH2:5][CH2:6][CH:7]([C:9](=[O:10])[CH3:1])[CH2:8]1.[CH3:3][C:4]1([CH3:11])[CH2:8][C:7]([CH:9]([OH:10])[CH3:1])=[CH:6][CH2:5]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 12673724HCID 12673724, compound

Product 2

HCID 19809724HCID 19809724, compoundHCID 19809727HCID 19809727, compoundYield 107%

Reagents, catalysts & solvents 2

HCID 6328Methyl iodideCatalystHCID 3283Diethyl EtherSolvent3×

Procedure

The starting 1-(3,3-dimethyl-1-cyclopentyl)-1-ethanone was prepared thus: 2.1 g (0.088 mol) of Mg, to which a few ml of ether had been added so as to cover it, were charged into a 250 ml vessel kept under nitrogen and around ten drops of CH3I were added thereto to trigger the reaction. Once the latter had started, what was left of 11.9 g of CH3I (0.084 mol) in 30 ml of ethyl ether was introduced while maintaining a slight reflux. The mixture was then heated to reflux for 1/2 h, cooled to room temperature and 10 g (0.08 mol) of 4,4-dimethyl-1-cyclopentene-1-carbaldehyde [prepared according to Magnusson et al., J. Org. Chem. 38, 1380 (1973)], in solution in 30 ml of ether, were added thereto. It was then re-heated to reflux for 1 h. After cooling, it was poured on ice and HCl, washed to neutrality with saturated NaCl, dried, filtered and concentrated under reduced pressure. After bulb-to-bulb distillation, 6 g (yield: 53.6%) of 1-(4,4-dimethyl-1-cyclopenten-1-yl)-1-ethanol were obtained, whose analytical data were the following:

Workup

  1. additionwere charged into a 250 ml vessel
  2. customthe reaction
  3. additionwas introduced
  4. temperaturewhile maintaining a slight reflux
  5. temperatureThe mixture was then heated
  6. temperatureto reflux for 1/2 h
  7. temperatureIt was then re-heated
  8. temperatureto reflux for 1 h
  9. temperatureAfter cooling
  10. washwashed
  11. customdried
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure
  14. distillationAfter bulb-to-bulb distillation

Sources & evidence

ORD record
ord-eae0d892ffac4ac0a6a0c580633ef464
Source dataset
uspto-grants-1992_11
Patent number
US05166412

Reaction notes

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