Acetic Acid → p-Chloro-beta-nitrostyrene
Reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[N+:10]([CH3:13])([O-:12])=[O:11].C[O-].[Na+].C(O)(=O)C.C(OC(=O)C)(=O)C>C1(C)C=CC=CC=1.CO>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:13][N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=1Participants
Conditions
- Temperature
- 2.5 °C
Procedure
To a solution of 57 g (98%, 0.397 mol) of 4-chlorobenzaldehyde and 24.8 g (0.398 mol) of nitromethane in 461 ml of toluene cooled to 5° C. were added 107.2 g of a solution of sodium methylate in methanol (30%; 0.596 mol) during 45 min. The mixture was subsequently stirred at 0 to 5° C. for 2 h. The suspension was cooled to 0° C. and then 40.0 g (0.666 mol) of anhydrous acetic acid were added, this causing the temperature to rise to 7° C. The mixture was diluted with 290 ml of toluene and methanol was removed by distillation at 100 mbar. 205 g (99%, 1.988 mol) of acetic anhydride were added, the mixture was heated to 50° C. and stirred for 15 h at this temperature. For workup, the mixture was poured onto 725 g of ice water, the phases were separated and the organic phase was extracted with alkaline water (pH 8.5). After concentration at 10 mbar, 74.8 g of the title compound in form of a yellow solid were obtained.
Workup
- temperatureThe suspension was cooled to 0° C.
- customto rise to 7° C
- customwas removed by distillation at 100 mbar
- temperaturethe mixture was heated to 50° C.
- stirringstirred for 15 h at this temperature
- customthe phases were separated
- extractionthe organic phase was extracted with alkaline water (pH 8.5)
- concentrationAfter concentration at 10 mbar, 74.8 g of the title compound in form of a yellow solid
- customwere obtained
Sources & evidence
- ORD record
- ord-f9f0cfa71ec7486c90041788134a8a88
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853455B2
Reaction notes
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