p-(Benzyloxy)nitrobenzene → 4-Benzyloxyaniline
Reaction equation
O.S.[Na].[CH2:4]([O:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(O)C>[CH2:4]([O:11][C:12]1[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Sodium hydrogen sulphide monohydrate (40 g) was added to a solution of 4-benzyloxynitrobenzene (25 g) in ethanol (800 ml) and the reaction mixture heated under reflux for four hours. The solvent was removed and the residue was treated with water and extracted into ether. The ether extract was dried and evaporated to give 4-benzyloxyaniline which was purified by extraction with hexane.
Workup
- temperaturethe reaction mixture heated
- temperatureunder reflux for four hours
- customThe solvent was removed
- additionthe residue was treated with water
- extractionextracted into ether
- extractionThe ether extract
- customwas dried
- customevaporated
Sources & evidence
- ORD record
- ord-1d8f28cc8c3f447fa021280b15636a6a
- Source dataset
- uspto-grants-1994_04
- Patent number
- US05302720
Reaction notes
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