1-Chloro-3-methyl-2-butene → Ethanone, 1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-
Reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([OH:9])[C:3]=1[C:10](=[O:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23]>O1CCCC1>[OH:1][C:2]1[C:7]([CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])=[C:6]([OH:8])[CH:5]=[C:4]([OH:9])[C:3]=1[C:10](=[O:12])[CH3:11]Participants
Procedure
In 250 ml of anhydrous tetrahydrofuran was dissolved 50.0 g of 2',4',6'-trihydroxyacetophenone, and 123.1 g of anhydrous potassium carbonate was added to the solution and the mixture was stirred at room temperature for 30 minutes. Then, 37.2 g of 1-chloro-3-methyl-2-butene was added dropwise to the mixture over a period of 20 minutes and reaction was carried out at room temperature for 24 hours. After the reaction, the reaction mixture was extracted with 2 l of ethyl acetate and the solvent was removed from the ethyl acetate layer by distillation, and the residue was recrystallized from a benzene/petroleum ether mixed solvent to obtain 38.6 g (yield=55.0%) of 2',4',6'-trihydroxy-3'-(3-methyl-2-butenyl)acetophenone in the form of a yellow prism.
Workup
- additionwas added to the solution
- customreaction
- waitwas carried out at room temperature for 24 hours
- customAfter the reaction
- extractionthe reaction mixture was extracted with 2 l of ethyl acetate
- customthe solvent was removed from the ethyl acetate layer by distillation
- customthe residue was recrystallized from a benzene/petroleum ether mixed solvent
Sources & evidence
- ORD record
- ord-52fba723316f4cd2bca05b04b53b574d
- Source dataset
- uspto-grants-1993_08
- Patent number
- US05234951
Reaction notes
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