Hydrochloric Acid → 1-(2-methoxyphenyl)-2-methylpropan-1-ol
Reaction equation
O1C[CH2:4][CH2:3][CH2:2]1.[CH3:6][O:7][C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=[O:11].C([Mg]Br)(C)C.Cl>O>[CH3:6][O:7][C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]([OH:11])[CH:3]([CH3:4])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Dry tetrahydrofuran (3 mL) was added to 1.01 g (7.43 mmol) of commercially available 2-methoxybenzaldehyde under nitrogen atmosphere, and the mixture was ice-cooled. To the mixture was added dropwise a 3.8 mL (7.6 mmol) of tetrahydrofuran solution containing 2 mol/L isopropyl-magnesium bromide. After completion of dropwise addition, the reaction mixture was stirred in an ice bath for 1 hour. The reaction mixture was poured into water, made acidic with diluted hydrochloric acid, and then, extracted with ether. The organic layers were combined, washed successively with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed, and the obtained residue was purified by silica gel column chromatography (Wako gel C-100, hexane-ethyl acetate, gradient) to obtain 1.00 g (5.56 mmol, Yield: 74.8%) of 1-(2-methoxyphenyl)-2-methyl-1-propanol.
Workup
- temperaturecooled
- additionAfter completion of dropwise addition
- extractionextracted with ether
- washwashed successively with water and brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was removed
- customthe obtained residue was purified by silica gel column chromatography (Wako gel C-100, hexane-ethyl acetate, gradient)
Sources & evidence
- ORD record
- ord-a7aaae1ec6cb47e89448a1b9883226cf
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07608563B2
Reaction notes
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