Potassium Carbonate → Ethyl 4-((3-formyl-4-nitrophenyl)oxy)butyrate
Reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].Br[CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:7]([C:6]1[CH:9]=[C:2]([O:1][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:3]=[CH:4][C:5]=1[N+:10]([O-:12])=[O:11])=[O:8]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 5-hydroxy-2-nitrobenzaldehyde (84.0 g) and ethyl 4-bromobutyrate (86 ml) in dry dimethylformamide (500 ml) blanketed under dry nitrogen was added potassium carbonate (76.0 g). The reaction mixture was heated to 100° C. for 1 hour. This mixture was cooled, and the solvent removed by evaporation to give a dark brown syrup. This residue was partitioned between ethyl acetate and saturated sodium carbonate (500 ml each). The organic layer was washed with additional saturated sodium carbonate (3×500 ml), and with brine (2×500 ml), dried, filtered and evaporated to give a dark brown syrup. Kugelrohr distillation (180° C., 0.2 mm) afforded ethyl 4-((3-formyl-4-nitrophenyl)oxy)butyrate (95 g) as a bright yellow syrup which slowly darkened upon standing.
Workup
- temperatureThis mixture was cooled
- customthe solvent removed by evaporation
- customto give a dark brown syrup
- customThis residue was partitioned between ethyl acetate and saturated sodium carbonate (500 ml each)
- washThe organic layer was washed with additional saturated sodium carbonate (3×500 ml)
- dry with materialwith brine (2×500 ml), dried
- filtrationfiltered
- customevaporated
- customto give a dark brown syrup
- distillationKugelrohr distillation (180° C., 0.2 mm)
Sources & evidence
- ORD record
- ord-b8b246c69564492589d09d1be72ae164
- Source dataset
- uspto-grants-1984_12
- Patent number
- US04490371
Reaction notes
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