Pyridinium chloride → 1-(3-Chloro-5-hydroxyphenyl)ethanone
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([O:8]C)[CH:7]=1.Cl.N1C=CC=CC=1>O>[Cl:1][C:2]1[CH:3]=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([OH:8])[CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 220 °C
Procedure
A mixture of 1-(3-chloro-5-methoxy-phenyl)-ethanone (14.3 g, 0.08 mol.) and pyridine hydrochloride (44.8 g, 0.39 mol.) was heated at 220° C. for 2 hrs. The mixture was poured into water (200 mL) and extracted with ethyl acetate (2×200 mL). The organic extracts were combined, washed with water (40 mL), brine (40 mL) and concentrated to give an oil. Flash Chromatography on Silica Get eluting with ethyl acetate/hexanes (1:1) gave 6.6 g solid. MS (m/e): 170/172 (M+).
Workup
- extractionextracted with ethyl acetate (2×200 mL)
- washwashed with water (40 mL), brine (40 mL)
- concentrationconcentrated
- customto give an oil
- customFlash Chromatography on Silica Get
- washeluting with ethyl acetate/hexanes (1:1)
Sources & evidence
- ORD record
- ord-8030c4362c1f454eb5725cd3a6d76016
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06380218B1
Reaction notes
Loading…