Ethyl bromoacetate → Ethyl (4-acetyl-3-hydroxy-2-propylphenoxy)acetate
Reaction equation
[CH3:1][CH2:2][CH2:3][C:4]1[C:9]([OH:10])=[C:8]([C:11]([CH3:13])=[O:12])[CH:7]=[CH:6][C:5]=1[OH:14].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[C:11]([C:8]1[CH:7]=[CH:6][C:5]([O:14][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:4]([CH2:3][CH2:2][CH3:1])[C:9]=1[OH:10])(=[O:12])[CH3:13]Participants
5
Procedure
A mixture of 3 g of 2,4-dihydroxy-3-propylacetophenone, 2.5 g of ethyl bromoacetate, 2.3 g of anhydrous potassium carbonate, and 30 ml of methyl ethyl ketone was refluxed for 5 hours. Then, the solvent was removed under reduced pressure and after addition of 50 ml of toluene, the mixture was washed with water, a diluted aqueous solution of sodium hydroxide, and water successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue thus formed was recrystallized from a mixture of toluene and n-hexane to provide 2.8 g of ethyl (4-acetyl-3-hydroxy-2-propylphenoxy)acetate (melting point: 66° to 66.5° C.).
Workup
- temperaturewas refluxed for 5 hours
- customThen, the solvent was removed under reduced pressure
- additionafter addition of 50 ml of toluene
- washthe mixture was washed with water
- dry with materiala diluted aqueous solution of sodium hydroxide, and water successively, dried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue thus formed
- customwas recrystallized from a mixture of toluene and n-hexane
Sources & evidence
- ORD record
- ord-a8bfe94816f144bbabc46eed1504d6ba
- Source dataset
- uspto-grants-1990_03
- Patent number
- US04908368
Reaction notes
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