1-(3-Chloro-2-hydroxy-5-methoxyphenyl)ethanone → 1-(3-Chloro-2,5-dihydroxyphenyl)ethanone
Reaction equation
[C:1]([C:4]1[C:5]([OH:13])=[C:6]([Cl:12])[CH:7]=[C:8]([O:10]C)[CH:9]=1)(=[O:3])[CH3:2]>Br>[C:1]([C:4]1[C:5]([OH:13])=[C:6]([Cl:12])[CH:7]=[C:8]([OH:10])[CH:9]=1)(=[O:3])[CH3:2]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
8.7 g of 3-acetyl-1-chloro-2-hydroxy-5-methoxybenzene were taken up in 150 ml of hydrobromic acid (48% strength in water). 1.69 g of red phosphorus were added, and the mixture was then stirred at 85° C. for 15 hours. After cooling, the reaction mixture was poured into about 1 liter of ice-cold water and extracted with ethyl acetate. The crude product obtained after drying and concentration of the ethyl acetate phase was purified by column chromatography. Yield: 2.9 g (36%)
Workup
- temperatureAfter cooling
- extractionextracted with ethyl acetate
Sources & evidence
- ORD record
- ord-3ee1e54211a449bb9ef331101732ebc7
- Source dataset
- uspto-grants-2005_09
- Patent number
- US06949551B2
Reaction notes
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