1-(3-Chlorophenyl)ethanone → Benzenemethanol, 3-chloro-alpha,alpha-dimethyl-
Reaction equation
[CH3:1][Mg]Br.[CH3:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=1)=[O:6]>CCOCC>[Cl:13][C:9]1[CH:8]=[C:7]([C:5]([OH:6])([CH3:1])[CH3:4])[CH:12]=[CH:11][CH:10]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Methylmagnesium bromide (3.6 mL, 10.67 mmol, Aldrich, 3 M solution in ether) was added to a cooled (−10° C.) solution of 3-chloroacetophenone (1.5 g, 9.7 mmol) in anhydrous ether slowly over 30 min. After complete addition, the reaction mixture was slowly warmed to room temperature, stirred for 18 hours. Again cooled (−5° C.), than quenched with sat. ammonium chloride solution over 30 min. The reaction mixture was extracted with ether, dried, filtered and concentrated to afford 1.55 g of 2-(3-chlorophenyl)propan-2-ol.
Workup
- additionAfter complete addition
- temperatureAgain cooled (−5° C.)
- customthan quenched with sat. ammonium chloride solution over 30 min
- extractionThe reaction mixture was extracted with ether
- customdried
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-908307a7f4c64e7bb57029ee691457c9
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07888366B2
Reaction notes
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