3-Isobutylbenzaldehyde → 1-(3-Isobutylphenyl)ethanol

HRID 249148Notes

Reaction equation

HRID 249148 reaction equation
[CH3:1][Mg]Br.[CH2:4]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=[O:12])[CH:5]([CH3:7])[CH3:6]>CCOCC.O1CCCC1>[CH2:4]([C:8]1[CH:9]=[C:10]([CH:11]([OH:12])[CH3:1])[CH:13]=[CH:14][CH:15]=1)[CH:5]([CH3:7])[CH3:6]

Participants

5

Reactant 2

HCID 220441763-IsobutylbenzaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 190247741-(3-Isobutylphenyl)ethanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of methylmagnesium bromide in ether (4 ml) was added to a solution of 3-isobutylbenzaldehyde (1.0 g) in tetrahydrofuran (10 ml) at 0° C. After stirred at 0° C. for 30 minutes, the mixture was partitioned between ether and 1N hydrochloric acid. The organic layer was separated, washed with water and brine, and dried over magnesium sulfate. After evaporation of the solvent, the residue was chromatographed on silica gel (30 g) eluting with a mixture of ethyl acetate and hexane (1:10) to give 1-(3-isobutylphenyl)ethanol (1.12 g) as an oil.

Workup

  1. customthe mixture was partitioned between ether and 1N hydrochloric acid
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvent
  6. customthe residue was chromatographed on silica gel (30 g)
  7. washeluting with a mixture of ethyl acetate and hexane (1:10)

Sources & evidence

ORD record
ord-b115d750318148fba635543265d9bbca
Source dataset
uspto-grants-1993_05
Patent number
US05212320

Reaction notes

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