Water → 2-Acetoxy-5-chlorobenzonitrile
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[C:7]#[N:8].S(=O)(=O)(O)O.O.[C:17](OC(=O)C)(=[O:19])[CH3:18]>>[C:17]([O:10][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:9][C:6]=1[C:7]#[N:8])(=[O:19])[CH3:18]Participants
Conditions
- Temperature
- 60 °C
Procedure
Further, 39.25 g (0.25 mol) of the 5-chloro-2-hydroxybenzonitrile were dissolved in 40 ml of acetic anhydride, followed by the addition of 0.5 ml of concentrated sulfuric acid. After the reaction mixture was heated at 60° C. for 10 minutes, water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with 1N NaOH and a saturated aqueous solution of sodium chloride and was then dried over Na2SO4. The solvent was distilled off under reduced pressure, whereby 45 g of 2-acetoxy-5-chlorobenzonitrile (yield: 92%). A mixture of 44 g of the 2-acetoxy-5-chlorobenzonitrile and 99 g (0.75 mol) of aluminum chloride was then heated at 160° C. for 3 hours. The reaction mixture was allowed to cool down to room temperature, and was then poured into ice water which contained 100 ml of concentrated hydrochloric acid. The slurry was extracted with ethyl acetate (3×350 ml). The extract was washed with 1N hydrochloric acid (3×200 ml) and a saturated aqueous solution of sodium chloride (400 ml) and was then dried over Na2SO4. The solvent was distilled off under reduced pressure. The residue was washed with dichloromethane to remove byproducts, and was then collected by filtration, whereby 16.5 g of the title compound were obtained as brown powder (yield: 38%).
Workup
- extractionfollowed by extraction with ethyl acetate
- washThe organic layer was washed with 1N NaOH
- dry with materiala saturated aqueous solution of sodium chloride and was then dried over Na2SO4
Sources & evidence
- ORD record
- ord-c9df0e4d35a04b9aa651529be7516c90
- Source dataset
- uspto-grants-2000_04
- Patent number
- US06046212
Reaction notes
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