3-Methylbutanal → α-(2-Methylpropyl)benzenemethanol

HRID 2293669Notes

Reaction equation

HRID 2293669 reaction equation
[CH:1](=[O:6])[CH2:2][CH:3]([CH3:5])[CH3:4].[C:7]1([Mg]Br)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Cl-].[NH4+]>C(OCC)C>[CH3:4][CH:3]([CH3:5])[CH2:2][CH:1]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[OH:6]

Participants

5

Reactant 3

HCID 115523-MethylbutanalHCID 25517Ammonium ChlorideHCID 178418255HCID 178418255, compound

Product 1

HCID 12487504α-(2-Methylpropyl)benzenemethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a time-dried flask under an argon atmosphere is added 0.50 mL of commercially available isovaleraldehyde and charged with 15 mL of diethyl ether. The solution is cooled to 0° C. and is treated with 2.0 mL (3.0 M in diethyl ether) of phenylmagnesium bromide. The reaction mixture is left to warm to room temperature overnight and then partioned between diethyl ether and saturated ammonium chloride. The aqueous phases are extracted with diethyl ether and the combined organic layers are dried (magnesium sulfate) and finally concentrated under reduced pressure. The residue is flash column chromatographed using 20% diethyl ether in hexanes to yield 800 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. extractionThe aqueous phases are extracted with diethyl ether
  4. dry with materialthe combined organic layers are dried (magnesium sulfate)
  5. concentrationfinally concentrated under reduced pressure
  6. customchromatographed

Sources & evidence

ORD record
ord-22c86a1ad8d14d528769043e69fd87ee
Source dataset
uspto-grants-1997_11
Patent number
US05686486

Reaction notes

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