2-Methoxybenzaldehyde → 1-(2-Methoxyphenyl)propan-1-ol
Reaction equation
[CH:1](=[O:10])[C:2]1[C:3]([O:8][CH3:9])=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH2:11]([Mg]Br)[CH3:12]>O1CCCC1>[CH3:9][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH:1]([OH:10])[CH2:11][CH3:12]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a time-dried flask containing a solution of o-anisaldehyde (2.00 g) in dry tetrahydrofuran (9.8 mL) at 0° C. under nitrogen is added a solution of ethylmagnesium bromide (3M in diethyl ether, 5.4 mL) in dry tetrahydrofuran (5.4 mL) over 25 min. The resulting mixture is stirred at 0° C. for 1 hr, quenched with saturated aqueous ammonium chloride (15 mL), and the layers are separated. The aqueous phase is extracted with diethyl ether (2×30 mL) and the combined organic phase is washed with saline (15 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give an oil which is then chromatographed on silica gel (230-400 mesh, 250 g), eluting with a gradient of ethyl acetate/hexane (5/95-10/90). Pooling of fractions having an Rf =0.44 by TLC (ethyl acetate/hexane, 25/75) and removal of solvent gives the title compound.
Workup
- customquenched with saturated aqueous ammonium chloride (15 mL)
- customthe layers are separated
- extractionThe aqueous phase is extracted with diethyl ether (2×30 mL)
- washthe combined organic phase is washed with saline (15 mL)
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customto give an oil which
- customis then chromatographed on silica gel (230-400 mesh, 250 g)
- washeluting with a gradient of ethyl acetate/hexane (5/95-10/90)
- customby TLC (ethyl acetate/hexane, 25/75) and removal of solvent
Sources & evidence
- ORD record
- ord-462bca7b1b0e40f9ac41b2571556e482
- Source dataset
- uspto-grants-1997_11
- Patent number
- US05686486
Reaction notes
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