Acetone → 2-Ethyl-2-prenyl-3-hexenol

HRID 1905621Notes

Reaction equation

HRID 1905621 reaction equation
CC([O-])C.CC([O-])C.CC([O-])C.[Al+3].[CH2:14]([C:16]([CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])([CH:19]=[CH:20][CH2:21][CH3:22])[CH:17]=[O:18])[CH3:15].CC(C)=O>C(O)(C)C>[CH2:14]([C:16]([CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])([CH:19]=[CH:20][CH2:21][CH3:22])[CH2:17][OH:18])[CH3:15]

Participants

5

Reactant 3

HCID 180AcetoneHCID 11143Aluminum isopropoxideHCID 542326252-Butenyl-2-ethyl-5-methyl hex-4-enal

Product 1

HCID 1744102-Ethyl-2-prenyl-3-hexenol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

Into a 2 liter four-neck flask, provided with stirrer, column, dropping funnel, and thermometer, 0.5 moles of aluminum isopropylate and 1 liter of dry isopropanol are first introduced. To the boiling mixture, a solution of 1 mole 2-ethyl-2-prenyl-3-hexenal, dissolved in 200 ml of dry isopropanol were added drop by drop. At all times, the reaction mixture was kept boiling to the extent that the acetone being formed could be withdrawn by the column. When in the distillate acetone could no longer be detected, the isopropanol was distilled off. Finally, the residue was poured into 250 ml of 20% hydrochloric acid, the phases were separate, and the organic phase was dried with calcium chloride. The desired product was then distilled over a Vigreux column.

Workup

  1. customInto a 2 liter four-neck flask, provided with stirrer
  2. additionwere added drop by drop
  3. customformed could
  4. custombe withdrawn by the column
  5. distillationthe isopropanol was distilled off
  6. additionFinally, the residue was poured into 250 ml of 20% hydrochloric acid
  7. customthe phases were separate
  8. dry with materialthe organic phase was dried with calcium chloride
  9. distillationThe desired product was then distilled over a Vigreux column

Sources & evidence

ORD record
ord-f5f4fe97563c4e5ab525223b3a964488
Source dataset
uspto-grants-1987_03
Patent number
US04647406

Reaction notes

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