Pyridinium chloride → 1-(3-Chloro-5-hydroxyphenyl)ethanone

HRID 844024Notes

Reaction equation

HRID 844024 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]=1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 134938543'-Chloro-5'-methoxyacetophenone

Product 1

HCID 226122241-(3-Chloro-5-hydroxyphenyl)ethanoneYield 48.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

  1. extractionextracted with ethyl acetate (2×200 mL)
  2. washwashed with water (40 mL), brine (40 mL)
  3. concentrationconcentrated
  4. customto give an oil
  5. customFlash Chromatography on Silica Get
  6. washeluting with ethyl acetate/hexanes (1:1)

Sources & evidence

ORD record
ord-8030c4362c1f454eb5725cd3a6d76016
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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