3-Aminophenol → 3-ethoxymethoxyphenylamine
Reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.[CH2:11]([O:13][CH2:14]Cl)[CH3:12]>C(#N)C>[CH2:11]([O:13][CH2:14][O:10][C:6]1[CH:5]=[C:4]([NH2:3])[CH:9]=[CH:8][CH:7]=1)[CH3:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
12 g (274.9 mmol) of a dispersion of sodium hydride (55% in oil) was added portionwise at 0° C. to a solution of 20.0 g (183.3 mmol) of 3-aminophenol in 450 mL of dried acetonitrile. The mixture was then allowed to agitate at 0° C. for 3 hours. A solution of 25 g (210.8 mmol) of chloromethyl ethyl ether in 30 mL of acetonitrile was added dropwise, and the mixture was allowed to agitate overnight at room temperature. The reaction mixture was then filtered and the filter cake was washed with a small amount of acetone and the filtrate was evaporated. This gave 32.3 g of 3-ethoxymethoxyphenylamine. The resulting product was used in the next step without further purification.
Workup
- stirringto agitate overnight at room temperature
- filtrationThe reaction mixture was then filtered
- washthe filter cake was washed with a small amount of acetone
- customthe filtrate was evaporated
- customThe resulting product was used in the next step without further purification
Sources & evidence
- ORD record
- ord-6ac75bfba4484f3fae43dcee6a8cae9c
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07128764B2
Reaction notes
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