2-(3,4-Dichlorophenyl)-1-phenylethanone → 3-(3,4-Dichlorophenyl)-2-phenyl-6-methylpyran-4-one
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10](=[O:11])[CH:9]=[C:4]([CH3:3])[O:11][C:10]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
To a solution of 3,4-dichlorophenylacetophenone (5.3 g; 20 mmoles) in glacial acetic acid (90 ml), polyphosphoric acid (64 g) was added and the resulting solution heated at 140° C. or 24 hours. After cooling, the reaction mixture was poured into ice-water, extracted with ethyl acetate (3×75 ml), the organic solution dried (Na2SO4) and the solvent removed under reduced pressure. The obtained residue was purified by column chromatography with silica gel and n-hexane-ethyl acetate 3:2 as eluent. 3-(3,4-dichlorophenyl)-2-phenyl-6-methylpyran-4-one (1.68 g) was obtained, m.p. 104° C.
Workup
- temperatureAfter cooling
- extractionextracted with ethyl acetate (3×75 ml)
- dry with materialthe organic solution dried (Na2SO4)
- customthe solvent removed under reduced pressure
- customThe obtained residue was purified by column chromatography with silica gel and n-hexane-ethyl acetate 3:2 as eluent
Sources & evidence
- ORD record
- ord-1e4a1b1093e44343a6c5822f41150efb
- Source dataset
- uspto-grants-2003_02
- Patent number
- US06518303B2
Reaction notes
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