4-Nitrophenol → Diethyl[2-(4-nitrophenoxy)ethyl]amine
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[O-]CC.[Na+].C(=O)([O-])[O-].[K+].[K+].Cl.[CH2:22]([N:24]([CH2:28][CH3:29])[CH2:25][CH2:26]Cl)[CH3:23]>C(O)C>[CH2:22]([N:24]([CH2:28][CH3:29])[CH2:25][CH2:26][O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[CH3:23]Participants
Procedure
A solution of 27.8 g (0.2 mol) of 4-nitrophenol in 500 ml of ethanol was treated with 15 g (0.22 mol) of sodium ethoxide. After stirring at room temperature for 30 minutes the solvent was removed under reduced pressure. The residual yellow solid was stirred in a mixture of 160 ml of xylene and 30 ml of water and then treated with 41.4 g (0.3 mol) of potassium carbonate and 34.4 g (0.2 mol) of 2-diethylaminoethyl chloride hydrochloride. The mixture was heated under reflux for 17 hours and filtered while hot. The filter residue was washed with hot xylene and the combined filtrate and washings were evaporated under reduced pressure. Distillation of the residue under a high vacuum gave 31.4 g (66%) of 4-[2-(diethylamino)ethoxy]-nitrobenzene as a liquid.
Workup
- customwas removed under reduced pressure
- stirringThe residual yellow solid was stirred in a mixture of 160 ml of xylene and 30 ml of water
- temperatureThe mixture was heated
- temperatureunder reflux for 17 hours
- filtrationfiltered while hot
- washThe filter residue was washed with hot xylene
- customthe combined filtrate and washings were evaporated under reduced pressure
- distillationDistillation of the residue under a high vacuum
Sources & evidence
- ORD record
- ord-a53ac69b22754b48ab572b63f98ef2e5
- Source dataset
- uspto-grants-2000_11
- Patent number
- US06150373
Reaction notes
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