N,N,N',N'-Tetramethylmethanediamine → 1-(4,5-Dimethoxy-2-methylphenyl)-2-phenylprop-2-en-1-one
Reaction equation
[C:1](OC(=O)C)(=O)C.[CH3:8][O:9][C:10]1[C:15]([O:16][CH3:17])=[CH:14][C:13]([C:18](=[O:26])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:12]([CH3:27])[CH:11]=1.CN(CN(C)C)C>O>[CH3:8][O:9][C:10]1[C:15]([O:16][CH3:17])=[CH:14][C:13]([C:18](=[O:26])[C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH2:1])=[C:12]([CH3:27])[CH:11]=1Participants
Procedure
240 ml of acetic anhydride are added dropwise in the course of 20 minutes at room temperature, while stirring, to a mixture of 135.0 g (0.50 mole) of 1-(4,5-dimethoxy-2-methylphenyl)-2-phenyl-1-ethanone and 250 ml of bis-(di-methylamino)-methane, the temperature being held at 40° by cooling with an ice bath. The reaction mixture is stirred at 40° for a further hour and is then poured into a 2 kg mixture of ice and water, during which the crude product crystallises. After stirring for 15 minutes at 15° the crude product is filtered off, the filtered material is washed with cold water and then dried for 18 hours at 30° under approximately 100 mbar, yielding 1-(4,5-dimethoxy-2-methylphenyl)-2-phenyl-2-propen-1-one having a melting point of 57°-59°.
Workup
- custombeing held at 40°
- temperatureby cooling with an ice bath
- customcrystallises
- stirringAfter stirring for 15 minutes at 15° the crude product
- filtrationis filtered off
- washthe filtered material is washed with cold water
- customdried for 18 hours at 30° under approximately 100 mbar
Sources & evidence
- ORD record
- ord-38eac1767c244691b0599060aca3400c
- Source dataset
- uspto-grants-1985_02
- Patent number
- US04500542
Reaction notes
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