4-Ethylbenzaldehyde → 4-Ethyl-α-propylbenzenemethanol

HRID 2293675Notes

Reaction equation

HRID 2293675 reaction equation
[CH2:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1)[CH3:2].[CH2:11]([Mg]Br)[CH2:12][CH3:13]>C(OCC)C>[CH2:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]([OH:8])[CH2:11][CH2:12][CH3:13])=[CH:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 208614-EthylbenzaldehydeHCID 178455851HCID 178455851, compound

Product 1

HCID 224869074-Ethyl-α-propylbenzenemethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a flame-dried flask under an argon atmosphere is added 0.69 mL of commercially available 4-ethylbenzaldehyde and charged with 15 mL of diethyl ether. The solution is cooled to 0° C. and is treated with 3.0 mL (2.0M in diethyl ether) of propylmagnesium bromide. The reaction mixture is left to warm to room temperature overnight and then quenched by the addition of aqueous ammonium chloride. After dilution with diethyl ether the phases are separated; the organic layer is washed with saturated ammonium chloride, dried (magnesium sulfate) and finally concentrated under reduced pressure. The residue is flash column chromatographed using 25% to 30% diethyl ether in hexane to yield 1.08 g of the title product as a clear, colorless oil.

Workup

  1. waitThe reaction mixture is left
  2. temperatureto warm to room temperature overnight
  3. customquenched by the addition of aqueous ammonium chloride
  4. customAfter dilution with diethyl ether the phases are separated
  5. washthe organic layer is washed with saturated ammonium chloride
  6. dry with materialdried (magnesium sulfate)
  7. concentrationfinally concentrated under reduced pressure
  8. customchromatographed

Sources & evidence

ORD record
ord-010768999b264906882c5e797d45e26d
Source dataset
uspto-grants-1997_11
Patent number
US05686486

Reaction notes

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