4-Nitrophenol → Ethyl 2-(4-nitrophenoxy)acetate
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].CN(C=O)C.Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>O.C(Cl)(Cl)Cl.CO>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:6][CH:5]=1)([O-:3])=[O:2]Participants
Conditions
- Temperature
- 70 °C
Procedure
Into a 50 mL 3-neck RBF equipped with a magnetic stirrer, reflux condenser, and thermo pocket were sequentially charged 4-nitro phenol (1.00 g), K2CO3 (1.98 g) and DMF (7 mL). The reaction mixture was heated to 70° C. for 15 minutes. Ethyl bromoacetate (1.44 g) was added at 70° C. and the reaction mixture was stirred at the same temperature for 30 minutes. The reaction was monitored on TLC using CHCl3:methanol (9.5:0.5) as mobile phase. After completion of the reaction, the mixture was cooled to room temperature and poured into cold water. Solid precipitate was filtered and washed with water. The solid was dried under reduced pressure at 45° C. for 1 hr to give 1.50 g of ethyl 2-(4-nitrophenoxy)acetate. The obtained solid was taken for the next step without further purification.
Workup
- customInto a 50 mL 3-neck RBF equipped with a magnetic stirrer
- temperaturereflux condenser
- customAfter completion of the reaction
- temperaturethe mixture was cooled to room temperature
- filtrationSolid precipitate was filtered
- washwashed with water
- customThe solid was dried under reduced pressure at 45° C. for 1 hr
Sources & evidence
- ORD record
- ord-c68220d34e054555bc0829143e7050d3
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09415049B2
Reaction notes
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