4-Nitrophenol → Butyl-4-nitrophenyl ether

To a solution of p-nitrophenol (56.0 g. 0.4 mole) in acetone (400 ml.) was added n-butyl bromide (60.0 g., 0.44 mole) and potassium carbonate (anhydrous, 56.0 g., 0.4 mole). The mixture was heated on the steam bath for 48.0 hours. The acetone was removed from the reaction mixture in vacuo. Then, water (400 ml.) was added to the residue, which was extracted twice with benzene (200 ml. portions). The benzene layers were washed thrice with 10% sodium hydroxide solution (150 ml. portions). The washed layers of benzene were then dried over anhydrous potassium carbonate and the solvent was removed in vacuo. The product obtained after evaporation of the solvent was a crude yellow liquid (63.0 g. 79%). This was used in Part B without further purification.

1. temperatureThe mixture was heated on the steam bath for 48.0 hours
2. customThe acetone was removed from the reaction mixture in vacuo
3. additionThen, water (400 ml.) was added to the residue, which
4. extractionwas extracted twice with benzene (200 ml. portions)
5. washThe benzene layers were washed thrice with 10% sodium hydroxide solution (150 ml. portions)
6. dry with materialThe washed layers of benzene were then dried over anhydrous potassium carbonate
7. customthe solvent was removed in vacuo
8. customThe product obtained
9. customafter evaporation of the solvent
10. customThis was used in Part B without further purification

ORD record

ord-e307fd90c4a844c7aa4519cf1844cb54

Source dataset

uspto-grants-1976_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US03947434