Acetic Acid → 1-(5-Chloro-2,4-dihydroxyphenyl)ethan-1-one
Reaction equation
[C:1]([OH:4])(=O)[CH3:2].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[OH:13]>B(F)(F)F.CCOCC>[Cl:5][C:6]1[C:7]([OH:13])=[CH:8][C:9]([OH:12])=[C:10]([C:1](=[O:4])[CH3:2])[CH:11]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
Acetic acid (17.5 ml) was added dropwise to a suspension of 4-chlorobenzene-1,3-diol (20 g, 0.138 mol) in BF3.OEt2 (100 ml) under a nitrogen atmosphere. The reaction mixture was stirred at 90° C. for 3.5 h and then allowed to cool to RT, causing a solid to precipitate. The mixture was poured into a 10% w/v aqueous sodium acetate solution (350 ml). This mixture was then stirred vigorously for 2.5 h to afford a light brown solid, which was filtered, washed with water, and air-dried overnight to afford the title compound 1-(5-chloro-2,4-dihydroxyphenyl)-ethanone (11.3 g, 44%).
Workup
- temperatureto cool to RT
- customto precipitate
- additionThe mixture was poured into a 10% w/v aqueous sodium acetate solution (350 ml)
- stirringThis mixture was then stirred vigorously for 2.5 h
- customto afford a light brown solid, which
- filtrationwas filtered
- washwashed with water
- customair-dried overnight
Sources & evidence
- ORD record
- ord-e5b6b3db390543f9a91bd74fb586dec4
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383616B2
Reaction notes
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