4-Methylbenzaldehyde → 4-Methyl-α-propylbenzenemethanol

HRID 2293673Notes

Reaction equation

HRID 2293673 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([CH:7]=[O:8])=[CH:3][CH:2]=1.[CH2:10]([Mg]Br)[CH2:11][CH3:12]>O1CCCC1>[CH3:9][C:1]1[CH:6]=[CH:5][C:4]([CH:7]([OH:8])[CH2:10][CH2:11][CH3:12])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 77254-MethylbenzaldehydeHCID 178455851HCID 178455851, compound

Product 1

HCID 954044-Methyl-α-propylbenzenemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a flame-dried flask under an argon atmosphere is added 0.59 mL of commercially available p-tolualdehyde and charged with 15 mL of tetrahydrofuran. 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, brine, dried (magnesium sulfate) and finally concentrated under reduced pressure. The residue is flash column chromatographed using 20% to 30% diethyl ether in hexane to yield 980 mg 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, brine
  6. dry with materialdried (magnesium sulfate)
  7. concentrationfinally concentrated under reduced pressure
  8. customchromatographed

Sources & evidence

ORD record
ord-82924f8cdc044494835f9988eea78261
Source dataset
uspto-grants-1997_11
Patent number
US05686486

Reaction notes

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