1,4-Dibromobutane → 3-(1-Pyrrolidinyl)phenol

A solution of m-aminophenol (12.6 gm, 0.115 moles) and 1,4-dibromobutane (50 gm, 0.23 moles) was heated to 130° C. for 12 hr. The mixture was cooled to room temperature and triturated with diethylether and then ethyl acetate. The residue was dissolved in ethyl acetate and extracted with 1M NaOH, water, and sat. NaCl. After drying the organic layer with MgSO4, filtering, and evaporating solvent under vacuum, the crude product was purified by silica gel chromatography to give a pale yellow solid. The solid was refluxed with 500 ml toluene and 17 ml triethylamine (0.12 moles) for one hr, cooled to room temperature and washed with water and sat. NaCl. The solution was dried again over MgSO4, filtered, and evaporated under vacuum to give 3-pyrrolidinylphenol as a white solid (6.0 gm, 0.037 moles, 32%).

1. customtriturated with diethylether
2. dissolutionThe residue was dissolved in ethyl acetate
3. extractionextracted with 1M NaOH, water, and sat. NaCl
4. dry with materialAfter drying the organic layer with MgSO4
5. filtrationfiltering
6. customevaporating solvent under vacuum
7. customthe crude product was purified by silica gel chromatography
8. customto give a pale yellow solid
9. temperaturecooled to room temperature
10. washwashed with water and sat. NaCl
11. dry with materialThe solution was dried again over MgSO4
12. filtrationfiltered
13. customevaporated under vacuum

ORD record

ord-a0598b9a66664f0fa97c2284ec29a7d8

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07550570B2