تفاعل #79478

معادلة التفاعل

triethylamine

m-aminophenol

1,4-dibromobutane

→

3-pyrrolidinylphenol

المردود 32.2%

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   أخرىtriturated with diethylether
2. 2
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
3. 3
   استخلاصextracted with 1M NaOH, water, and sat. NaCl
4. 4
   تجفيفAfter drying the organic layer with MgSO4
5. 5
   ترشيحfiltering
6. 6
   أخرىevaporating solvent under vacuum
7. 7
   أخرىthe crude product was purified by silica gel chromatography
8. 8
   أخرىto give a pale yellow solid
9. 9
   درجة الحرارةcooled to room temperature
10. 10
    غسيلwashed with water and sat. NaCl
11. 11
    تجفيفThe solution was dried again over MgSO4
12. 12
    ترشيحfiltered
13. 13
    أخرىevaporated under vacuum

الإجراء التجريبي

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%).

المصدر