2-[2-[2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol

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

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

Procedure: Dissolve one equivalet of sodium in at least 5 equivalents of tetraethylene glycol and then add one equivalent of triethylene glycol monobenzenesulfonate. Heat the resulting solution at 100° to 150° C. until the elimination of sodium benzene sulfontate is substantially complete. Remove the insoluble sulfonate salt by filtration and fractionally distill the resultiing product in vacuo to obtain heptaethylene glycol as the higher boiling fraction. Remove the insoluble sulfonate salt by filtration fractionally distill the resultiing product in vacuo

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

Procedure: Dissolve one equivalet of sodium in at least 5 equivalents of tetraethylene glycol and then add one equivalent of triethylene glycol monobenzenesulfonate. Heat the resulting solution at 100° to 150° C. until the elimination of sodium benzene sulfontate is substantially complete. Remove the insoluble sulfonate salt by filtration and fractionally distill the resultiing product in vacuo to obtain heptaethylene glycol as the higher boiling fraction. Remove the insoluble sulfonate salt by filtration fractionally distill the resultiing product in vacuo

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

Procedure: Dissolve one equivalet of sodium in at least 5 equivalents of tetraethylene glycol and then add one equivalent of triethylene glycol monobenzenesulfonate. Heat the resulting solution at 100° to 150° C. until the elimination of sodium benzene sulfontate is substantially complete. Remove the insoluble sulfonate salt by filtration and fractionally distill the resultiing product in vacuo to obtain heptaethylene glycol as the higher boiling fraction. Remove the insoluble sulfonate salt by filtration fractionally distill the resultiing product in vacuo

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

Procedure: To a solution of non-polydispersed tetraethylene glycol (51.5 g, 0.27 mol) in THF (1 L) was added potassium t-butoxide (14.8 g, 0.13 mol, small portions over ˜30 min). The reaction mixture was then stirred for 1 h and then 24 (29.15 g, 0.12 mol) dissolved in THF (90 mL) was added dropwise and the reaction mixture was stirred overnight. The crude reaction mixture was filtered through Celite (washed CH2Cl2, ˜200 mL) and evaporated to dryness. The oil was then dissolved in HCl (250 mL, 1 N) and washed with ethyl acetate (250 mL) to remove excess 24. Additional washings of ethyl acetate (125 mL) may be required to remove remaining 24. The aqueous phase was washed repetitively with CH2Cl2 (125 mL volumes) until most of the 25 has been removed from the aqueous phase. The first extraction will contain 24, 25, and dicoupled side product and should be back extracted with HCl (125 mL, 1N). The organic layers were combined and evaporated to dryness. The resultant oil was then dissolved in CH2Cl2 (100 mL) and washed repetitively with H2O (50 mL volumes) until 25 was removed. The aqueous fractions were combined, total volume 500 mL, and NaCl was added until the solution became cloudy and then was washed with CH2Cl2 (2×500 mL). The organic layers were combined, dried MgSO4, and evaporated to dryness to afford a the non-polydispersed title compound as an oil (16.9 g, 41% yield). It may be desirable to repeat one or more steps of the purification procedure to ensure high purity. was added dropwise the reaction mixture was stirred overnight The crude reaction mixture was filtered through Celite (washed CH2Cl2, ˜200 mL) evaporated to dryness The oil was then dissolved in HCl (250 mL, 1 N) washed with ethyl acetate (250 mL) to remove excess 24 to remove The aqueous phase was washed repetitively with CH2Cl2 (125 mL volumes) until most of the 25 has been removed from the aqueous phase The first extraction should be back extracted with HCl (125 mL, 1N) evaporated to dryness The resultant oil was then dissolved in CH2Cl2 (100 mL) washed repetitively with H2O (50 mL volumes) until 25 was removed total volume 500 mL, and NaCl was added until the solution was washed with CH2Cl2 (2×500 mL) dried MgSO4, and evaporated to dryness

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

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

Procedure: To a solution of non-polydispersed tetraethylene glycol (51.5 g, 0.27 mol) in THF (1 L) was added potassium t-butoxide (14.8 g, 0.13 mol, small portions over ˜30 min). The reaction mixture was then stirred for 1 h and then 24 (29.15 g, 0.12 mol) dissolved in THF (90 mL) was added dropwise and the reaction mixture was stirred overnight. The crude reaction mixture was filtered through Celite (washed CH2Cl2, ˜200 mL) and evaporated to dryness. The oil was then dissolved in HCl (250 mL, 1 N) and washed with ethyl acetate (250 mL) to remove excess 24. Additional washings of ethyl acetate (125 mL) may be required to remove remaining 24. The aqueous phase was washed repetitively with CH2Cl2 (125 mL volumes) until most of the 25 has been removed from the aqueous phase. The first extraction will contain 24, 25, and dicoupled side product and should be back extracted with HCl (125 mL, 1N). The organic layers were combined and evaporated to dryness. The resultant oil was then dissolved in CH2Cl2 (100 mL) and washed repetitively with H2O (50 mL volumes) until 25 was removed. The aqueous fractions were combined, total volume 500 mL, and NaCl was added until the solution became cloudy and then was washed with CH2Cl2 (2×500 mL). The organic layers were combined, dried MgSO4, and evaporated to dryness to afford a the non-polydispersed title compound as an oil (16.9 g, 41% yield). It may be desirable to repeat one or more steps of the purification procedure to ensure high purity. was added dropwise the reaction mixture was stirred overnight The crude reaction mixture was filtered through Celite (washed CH2Cl2, ˜200 mL) evaporated to dryness The oil was then dissolved in HCl (250 mL, 1 N) washed with ethyl acetate (250 mL) to remove excess 24 to remove The aqueous phase was washed repetitively with CH2Cl2 (125 mL volumes) until most of the 25 has been removed from the aqueous phase The first extraction should be back extracted with HCl (125 mL, 1N) evaporated to dryness The resultant oil was then dissolved in CH2Cl2 (100 mL) washed repetitively with H2O (50 mL volumes) until 25 was removed total volume 500 mL, and NaCl was added until the solution was washed with CH2Cl2 (2×500 mL) dried MgSO4, and evaporated to dryness

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

Procedure: Dissolve one equivalent of sodium in at least 5 equivalents of tetraethylene glycol and then add one equivalent of triethylene glycol monobenzenesulfonate. Heat the resulting solution at 100° to 150°C until the elimination of sodium benzene sulfonate is substantially complete. Remove the insoluble sulfonate salt by filtration and fractionally distill the resulting product in vacuo to obtain heptaethylene glycol as the higher boiling fraction. Remove the insoluble sulfonate salt by filtration fractionally distill the resulting product in vacuo

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

Procedure: Dissolve one equivalet of sodium in at least 5 equivalents of tetraethylene glycol and then add one equivalent of triethylene glycol monobenzenesulfonate. Heat the resulting solution at 100° to 150° C. until the elimination of sodium benzene sulfontate is substantially complete. Remove the insoluble sulfonate salt by filtration and fractionally distill the resultiing product in vacuo to obtain heptaethylene glycol as the higher boiling fraction. Remove the insoluble sulfonate salt by filtration fractionally distill the resultiing product in vacuo

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

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

Procedure: To a solution of non-polydispersed tetraethylene glycol (51.5 g, 0.27 mol) in THF (1 L) was added potassium t-butoxide (14.8 g, 0.13 mol, small portions over ˜30 min). The reaction mixture was then stirred for 1 h and then 24 (29.15 g, 0.12 mol) dissolved in THF (90 mL) was added dropwise and the reaction mixture was stirred overnight. The crude reaction mixture was filtered through Celite (washed CH2Cl2, ˜200 mL) and evaporated to dryness. The oil was then dissolved in HCl (250 mL, 1 N) and washed with ethyl acetate (250 mL) to remove excess 24. Additional washings of ethyl acetate (125 mL) may be required to remove remaining 24. The aqueous phase was washed repetitively with CH2Cl2 (125 mL volumes) until most of the 25 has been removed from the aqueous phase. The first extraction will contain 24, 25, and dicoupled side product and should be back extracted with HCl (125 mL, 1N). The organic layers were combined and evaporated to dryness. The resultant oil was then dissolved in CH2Cl2 (100 mL) and washed repetitively with H2O (50 mL volumes) until 25 was removed. The aqueous fractions were combined, total volume 500 mL, and NaCl was added until the solution became cloudy and then was washed with CH2Cl2 (2×500 mL). The organic layers were combined, dried MgSO4, and evaporated to dryness to afford a the non-polydispersed title compound as an oil (16.9 g, 41% yield). It may be desirable to repeat one or more steps of the purification procedure to ensure high purity. was added dropwise the reaction mixture was stirred overnight The crude reaction mixture was filtered through Celite (washed CH2Cl2, ˜200 mL) evaporated to dryness The oil was then dissolved in HCl (250 mL, 1 N) washed with ethyl acetate (250 mL) to remove excess 24 to remove The aqueous phase was washed repetitively with CH2Cl2 (125 mL volumes) until most of the 25 has been removed from the aqueous phase The first extraction should be back extracted with HCl (125 mL, 1N) evaporated to dryness The resultant oil was then dissolved in CH2Cl2 (100 mL) washed repetitively with H2O (50 mL volumes) until 25 was removed total volume 500 mL, and NaCl was added until the solution was washed with CH2Cl2 (2×500 mL) dried MgSO4, and evaporated to dryness