methyl 7-oxabicyclo[4.1.0]heptane-3-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 3-neck 100 mL flask equipped with an argon inlet, stir bar and distillation apparatus was added 1-octadecanol (5.03 g, 19 mmol, obtained from Sigma-Aldrich), methyl 3,4-epoxycyclohexanecarboxylate (ERL-4140, 8.69 g, 56 mmol, obtained from Dow Chemical Company), 1,4-diazabicyclo[2.2.2]octane (DABCO™, 1.02 g, 9.1 mmol, obtained from Sigma-Aldrich) and toluene (15 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 (15 mL) and washed with brine (3×15 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 6.78 g (87%) of a white solid (mp=32-34° C.) of octadecyl 3,4-epoxycyclohexanecarboxylate. 1H NMR (CDCl3, δ): 4.06 (td, J=6.7, 1.9 Hz, 2H), 3.25-3.14 (m, 2H), 2.55-2.45 (m, 1H), 2.31-1.26 (m, 38H), 0.88 (t, J=6.7 Hz, 3H). To a 3-neck 100 mL flask equipped with an argon inlet distillation apparatus ceased collecting in the receiving flask The still pot from the distillation was diluted with toluene (15 mL) washed with brine (3×15 mL) The organic layer was separated dried over MgSO4 filtered The solvent was removed in vacuo The excess methyl 3,4-epoxycyclohexane carboxylate was removed via Kugelrohr distillation under reduced vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). To a 3-neck 250 mL flask equipped with an argon inlet distillation apparatus ceased collecting in the receiving flask The still pot from the distillation was diluted with toluene (60 mL) washed with brine (3×60 mL) The organic layer was separated dried over MgSO4 filtered The solvent was removed in vacuo The excess methyl 3,4-epoxycyclohexane carboxylate was removed via Kugelrohr distillation under reduced vacuum

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:107.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 3,4-epoxycyclohexanecarboxylate (50 g), and tripropylene glycol (33.8 g) in 60 milliliters (“mL”) of heptane were heated in a flask equipped with a 120-mL insulated Vigreaux column, Dean-Stark trap, drying tube and magnetic stirrer. The Dean-Stark trap was pre-filled with heptane. After refluxing the heptane for 60 minutes to azeotropically remove any water moisture, 0.0340 g of anhydrous sodium acetate (406 ppm by weight based on undiluted starting materials) was added as a transesterification catalyst. Methanol/heptane azeotrope was collected in the Dean-Stark trap and heating was continued for 405 minutes. The reaction temperature gradually increased from 102 to 113° C. during the course of the reaction, and the lower (methanol-rich) layer had a volume of 20.2 mL. Heating was continued and a nitrogen sparge was used to help remove any remaining heptane solvent by distillation. The product was allowed to cool to room temperature. The product consisted of 86 wt % of the mono and diepoxide adducts of tripropylene glycol, 0.8 wt % residual monoepoxide, and 14 wt % higher oligomers by uncorrected size-exclusion chromatography using THF solvent and a refractive index detector. Purity by gas chromatography was 88%. The viscosity of the product was 380 centipoise (cP) and the epoxy equivalent weight (titration) was 245 (theoretical 230). The product resin was formulated into a photo-crosslinkable material without further purification. equipped with a 120-mL drying tube and magnetic stirrer The Dean-Stark trap was pre-filled with heptane After refluxing the heptane for 60 minutes to azeotropically remove any water moisture, 0.0340 g of anhydrous sodium acetate (406 ppm by weight based on undiluted starting materials) was added as a transesterification catalyst Methanol/heptane azeotrope was collected in the Dean-Stark trap heating Heating a nitrogen sparge to help remove any remaining heptane solvent by distillation to cool to room temperature The product resin was formulated into a photo-crosslinkable material without further purification

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 3-neck 100 mL flask equipped with an argon inlet, stir bar and distillation apparatus was added 1-octadecanol (5.03 g, 19 mmol, obtained from Sigma-Aldrich), methyl 3,4-epoxycyclohexanecarboxylate (ERL-4140, 8.69 g, 56 mmol, obtained from Dow Chemical Company), 1,4-diazabicyclo[2.2.2]octane (DABCO™, 1.02 g, 9.1 mmol, obtained from Sigma-Aldrich) and toluene (15 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 (15 mL) and washed with brine (3×15 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 6.78 g (87%) of a white solid (mp=32-34° C.) of octadecyl 3,4-epoxycyclohexanecarboxylate. 1H NMR (CDCl3, δ): 4.06 (td, J=6.7, 1.9 Hz, 2H), 3.25-3.14 (m, 2H), 2.55-2.45 (m, 1H), 2.31-1.26 (m, 38H), 0.88 (t, J=6.7 Hz, 3H). To a 3-neck 100 mL flask equipped with an argon inlet distillation apparatus ceased collecting in the receiving flask The still pot from the distillation was diluted with toluene (15 mL) washed with brine (3×15 mL) The organic layer was separated dried over MgSO4 filtered The solvent was removed in vacuo The excess methyl 3,4-epoxycyclohexane carboxylate was removed via Kugelrohr distillation under reduced vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). To a 3-neck 250 mL flask equipped with an argon inlet distillation apparatus ceased collecting in the receiving flask The still pot from the distillation was diluted with toluene (60 mL) washed with brine (3×60 mL) The organic layer was separated dried over MgSO4 filtered The solvent was removed in vacuo The excess methyl 3,4-epoxycyclohexane carboxylate was removed via Kugelrohr distillation under reduced vacuum