Tetraethyleneglycol monooctyl ether

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Tetraethyleneglycol (1243 g, 6.40 mol) was heated at 100° C. for 30 minutes with stirring and vigorous N2 bubbling, then cooled to 60° C. A 50% NaOH solution (70.4 g, 0.88 mol) was added and the resulting solution was heated at 100°-105° C. for 30 minutes with N2 bubbling. The solution was cooled to 60° C., bromooctane (154 g, 0.80 mol) was added, and the reaction was heated at 100°-110° C. for 24 hours. The reaction solution was cooled, added to ice water and extracted twice with methylene chloride. The combined extracts were washed with 10% NaOH, water and brine; dried, treated with charcoal, and filtered through a thin silica gel pad. The solvent was removed in vacuo; the residual product (155 g, 63%) was a pale yellow oil. the reaction was heated at 100°-110° C. for 24 hours The reaction solution was cooled extracted twice with methylene chloride The combined extracts were washed with 10% NaOH, water and brine dried treated with charcoal filtered through a thin silica gel pad The solvent was removed in vacuo

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Tetraethyleneglycol (1243 g, 6.40 mol) was heated at 100° C. for 30 minutes with stirring and vigorous N2 bubbling, then cooled to 60° C. A 50% NaOH solution (70.4 g, 0.88 mol) was added and the resulting solution was heated at 100°-105° C. for 30 minutes with N2 bubbling. The solution was cooled to 60° C., bromooctane (154 g, 0.80 mol) was added, and the reaction was heated at 100°-110° C. for 24 hours. The reaction solution was cooled, added to ice water and extracted twice with methylene chloride. The combined extracts were washed with 10% NaOH, water and brine; dried, treated with charcoal, and filtered through a thin silica gel pad. The solvent was removed in vacuo; the residual product (155 g, 63%) was a pale yellow oil. the reaction was heated at 100°-110° C. for 24 hours The reaction solution was cooled extracted twice with methylene chloride The combined extracts were washed with 10% NaOH, water and brine dried treated with charcoal filtered through a thin silica gel pad The solvent was removed in vacuo

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Tetraethyleneglycol (1243 g, 6.40 mol) was heated at 100° C. for 30 minutes with stirring and vigorous N2 bubbling, then cooled to 60° C. A 50% NaOH solution (70.4 g, 0.88 mol) was added and the resulting solution was heated at 100°-105° C. for 30 minutes with N2 bubbling. The solution was cooled to 60° C., bromooctane (154 g, 0.80 mol) was added, and the reaction was heated at 100°-110° C. for 24 hours. The reaction solution was cooled, added to ice water and extracted twice with methylene chloride. The combined extracts were washed with 10% NaOH, water and brine; dried, treated with charcoal, and filtered through a thin silica gel pad. The solvent was removed in vacuo; the residual product (155 g, 63%) was a pale yellow oil. the reaction was heated at 100°-110° C. for 24 hours The reaction solution was cooled extracted twice with methylene chloride The combined extracts were washed with 10% NaOH, water and brine dried treated with charcoal filtered through a thin silica gel pad The solvent was removed in vacuo