4'-Hydroxyacetophenone → 1-{4-[2-(4-Chlorophenyl)ethoxy]phenyl}ethanone
Reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].S(O[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)(=O)(=O)C>CN(C=O)C>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][CH2:22][O:1][C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=2)=[CH:25][CH:26]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a stirred solution of 4′-hydroxyacetophenone (2.2 mmol) in DMF (5 mL) at rt, solid potassium carbonate (9.0 mmol) was added. 4-chlorophenethyl mesylate (2.0 mmol) was added to the reaction mixture and heated to 80° C. until completion according to General Procedure Q1, as indicated by TLC or HPLC. After cooling to rt, the reaction mixture was quenched using cold water (20 ml) and the product was isolated in EtOAc (2×20 ml). The combined organic layers were washed with saturated sodium bicarbonate (2×10 ml), water (2×10 ml) and brine (15 ml). The organic layer was dried over magnesium sulfate, and the solvent was removed in vacuuo to afford the desired 1-{4-[2-(4-chlorophenyl)ethoxy]phenyl}ethanone. The crude alkylated acetophenone was used for further transformation.
Workup
- temperatureAfter cooling to rt
- customthe reaction mixture was quenched
- customthe product was isolated in EtOAc (2×20 ml)
- washThe combined organic layers were washed with saturated sodium bicarbonate (2×10 ml), water (2×10 ml) and brine (15 ml)
- dry with materialThe organic layer was dried over magnesium sulfate
- customthe solvent was removed in vacuuo
Sources & evidence
- ORD record
- ord-46a00c7607d74c0486c3634f9a6c5c5f
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07361678B2
Reaction notes
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