Toluene → 4-Chloro-4'-methoxybutyrophenone
Reaction equation
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC=CC=1.[Cl:16][CH2:17][CH2:18][CH2:19][C:20](Cl)=[O:21]>>[Cl:16][CH2:17][CH2:18][CH2:19][C:20]([C:4]1[CH:5]=[CH:6][C:1]([O:7][CH3:8])=[CH:2][CH:3]=1)=[O:21]Participants
4
Conditions
- Temperature
- -10 °C
Procedure
To a cooled solution of 10.8 g (0.1 mol) anisole in 100 ml anhydrous toluene 13.3 g (0.1 mol) aluminium trichloride was added in portions over 15 minutes at −10° C. then 15.5 g (12.3 ml, 0.1 mmol) 4-chloro-butyryl chloride were added over 15 minutes keeping the temperature at −10° C. After stirring for additional 30 minutes at −10° C. the reaction mixture was hydrolyzed and the layers were separated. The aqueous layer was extracted with toluene (three times 100 ml) and the combined organic layers were dried and evaporated to yield 20.8 g (97%) 4-chloro-1-(4-methoxy-phenyl)-butan-1-one as a light beige liquid that solidified on standing. The product was used without further purification.
Workup
- customat −10° C
- customthe layers were separated
- extractionThe aqueous layer was extracted with toluene (three times 100 ml)
- customthe combined organic layers were dried
- customevaporated
Sources & evidence
- ORD record
- ord-b118ea003b0d422cbbcaa1deda55d693
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07288557B2
Reaction notes
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