تفاعل #727209

معادلة التفاعل

1-nonanol

methyl 3,4-epoxycyclohexanecarboxylate

1,4-diazabicyclo[2.2.2]octane

toluene

→

nonyl-3,4-epoxycylohexanecarboxylate

المذيبات

methanol

ظروف التفاعل

المعالجة

1. 1
   أخرىTo a 3-neck 250 mL flask equipped with an argon inlet
2. 2
   workup.DISTILLATIONdistillation apparatus
3. 3
   أخرىceased collecting in the receiving flask
4. 4
   workup.DISTILLATIONThe still pot from the distillation
5. 5
   workup.ADDITIONwas diluted with toluene (60 mL)
6. 6
   غسيلwashed with brine (3×60 mL)
7. 7
   أخرىThe organic layer was separated
8. 8
   تجفيفdried over MgSO4
9. 9
   ترشيحfiltered
10. 10
    أخرىThe solvent was removed in vacuo
11. 11
    أخرىThe excess methyl 3,4-epoxycyclohexane carboxylate was removed via Kugelrohr distillation under reduced vacuum

الإجراء التجريبي

To a 3-neck 250 mL flask equipped with an argon inlet, stir bar and distillation apparatus was added 1-nonanol (19.99 g, 0.14 mol, obtained from Sigma-Aldrich), methyl 3,4-epoxycyclohexanecarboxylate (ERL-4140, 23.80 g, 0.15 mol, obtained from Dow Chemical Company), 1,4-diazabicyclo[2.2.2]octane (DABCO™, 3.96 g, 35 mmol, obtained from Sigma-Aldrich) and toluene (60 mL). The reaction mixture was refluxed until methanol ceased collecting in the receiving flask and the completion of the reaction was confirmed by 1H NMR spectroscopy. The still pot from the distillation was diluted with toluene (60 mL) and washed with brine (3×60 mL). The organic layer was separated, dried over MgSO4 and filtered. The solvent was removed in vacuo. The excess methyl 3,4-epoxycyclohexane carboxylate was removed via Kugelrohr distillation under reduced vacuum to give 33.39 g (90%) of a clear, colorless oil of nonyl-3,4-epoxycylohexanecarboxylate 1H NMR (CDCl3, δ): 4.06 (td, J=6.7, 1.9 Hz, 2H), 3.25-3.10 (m, 2H), 2.55-2.42 (m, 1H), 2.31-1.27 (m, 20H), 0.88 (t, J=6.7 Hz, 3H).

المصدر