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

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: A solution of nonaethylene glycol benzyl methyl ether (10 g, 19.3 mmol) in ethanol (200 mL) was shaken with 10% palladium on activated charcal (Aldrich, 1.0 g) under hydrogen (50 psi) on a Parr apparatus for 3 h. The catalyst was filtered off (Celite), and the filtrate was concentrated in vacuo and dried by evaporation of toluene to provide nonaethylene glycol monomethyl ether as an oil (8.17 g, 99%). 1H-NMR (300 MHz, DMSO-d6) δ: 4.56 (t, 1H OH), 3.60-3.35 (m, 36H, 18 OCH2), 3.22 (s, 3H, CH3). The catalyst was filtered off (Celite) the filtrate was concentrated in vacuo dried by evaporation of toluene

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

Procedure: To a solution of nonaethylene glycol monomethyl ether (2.0 g. 4.7 mmol) in pyridine (15 mL) at 0° C. was added toluenesulfonyl chloride (1.35 g). After stiring at room temperature ovemight, the mixture was cooled to 0° and adjusted to pH 2 by addition of 12N HCl. Water (200 mL) was added and the solution was washed with methylene chloride (3×50 mL). The combined organic layers were washed with brine, dried (magnesium sulfate) and evaporated to provide nonaethylene glycol methyl tosyl ether as a colorless oil (2.7 g); 1H-NMR (DMSO-d6) δ: 7.85 and 7.55 (2d, 4, C6H4), 4.18 (m, 2, CH2OTos), 3.7-3.45 (m 34, 17 CH2), 3.2 (s, 3, OCH3) 2.40 (s, 3, CH3). After stiring at room temperature the mixture was cooled to 0° the solution was washed with methylene chloride (3×50 mL) The combined organic layers were washed with brine dried (magnesium sulfate) evaporated

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

Procedure: To a solution of nonaethylene glycol monomethyl ether (2.0 g. 4.7 mmol) in pyridine (15 mL) at 0° C. was added toluenesulfonyl chloride (1.35 g). After stiring at room temperature ovemight, the mixture was cooled to 0° and adjusted to pH 2 by addition of 12N HCl. Water (200 mL) was added and the solution was washed with methylene chloride (3×50 mL). The combined organic layers were washed with brine, dried (magnesium sulfate) and evaporated to provide nonaethylene glycol methyl tosyl ether as a colorless oil (2.7 g); 1H-NMR (DMSO-d6) δ: 7.85 and 7.55 (2d, 4, C6H4), 4.18 (m, 2, CH2OTos), 3.7-3.45 (m 34, 17 CH2), 3.2 (s, 3, OCH3) 2.40 (s, 3, CH3). After stiring at room temperature the mixture was cooled to 0° the solution was washed with methylene chloride (3×50 mL) The combined organic layers were washed with brine dried (magnesium sulfate) evaporated

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

Procedure: A solution of nonaethylene glycol benzyl methyl ether (10 g, 19.3 mmol) in ethanol (200 mL) was shaken with 10% palladium on activated charcal (Aldrich, 1.0 g) under hydrogen at 344.7 kPa (50 psi) on a Parr apparatus for 3 h. The catalyst was filtered off (Celite™), and the filtrate was concentrated in vacuo and dried by evaporation of toluene to provide nonaethylene glycol monomethyl ether as an oil (8.17 g, 99%), 1H-NMR (DMSO-d6) δ: 4.56 (t, 1 OH), 3.60-3.35 (m, 36, 18 OCH2), 3.22 (s, 3, CH3). The catalyst was filtered off (Celite™) the filtrate was concentrated in vacuo dried by evaporation of toluene

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

Procedure: A solution of nonaethylene glycol benzyl methyl ether (10 g, 19.3 mmol) in ethanol (200 mL) was shaken with 10% palladium on activated charcal (Aldrich, 1.0 g) under hydrogen at 344.7 kPa (50 psi) on a Parr apparatus for 3 h. The catalyst was filtered off (Celite™), and the filtrate was concentrated in vacuo and dried by evaporation of toluene to provide nonaethylene glycol monomethyl ether as an oil (8.17 g, 99%), 1H-NMR (DMSO-d6) δ: 4.56 (t, 1 OH), 3.60-3.35 (m, 36, 18 OCH2), 3.22 (s, 3, CH3). The catalyst was filtered off (Celite™) the filtrate was concentrated in vacuo dried by evaporation of toluene

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

Procedure: A solution of nonaethylene glycol benzyl methyl ether from above (38 g) in methanol (200 ml) was shaken with 10% palladium on activated charcal (Aldrich, 1.0 g) under hydrogen 344.7 kPa (50 psi) on a Parr apparatus overnight. The catalyst was filtered off (Celite™), and the filtrate was concentrated in vacuo to provide nonaethylene glycol monomethyl ether as an oil (23 g, 74%), 1H-NMR (CDCl3) δ: 3.67-3.47 (m, 36, 18 OCH2), 3.32 (s, 3, CH3). The catalyst was filtered off (Celite™) the filtrate was concentrated in vacuo

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

Procedure: A solution of nonaethylene glycol benzyl methyl ether from above (38 g) in methanol (200 ml) was shaken with 10% palladium on activated charcal (Aldrich, 1.0 g) under hydrogen 344.7 kPa (50 psi) on a Parr apparatus overnight. The catalyst was filtered off (Celite™), and the filtrate was concentrated in vacuo to provide nonaethylene glycol monomethyl ether as an oil (23 g, 74%), 1H-NMR (CDCl3) δ: 3.67-3.47 (m, 36, 18 OCH2), 3.32 (s, 3, CH3). The catalyst was filtered off (Celite™) the filtrate was concentrated in vacuo

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

Procedure: To a solution of nonaethylene glycol monomethyl ether (2.0 g. 4.7 mmol) in pyridine (15 mL) at 0° C. was added toluenesulfonyl chloride (1.35 g). After stiring at room temperature overnight, the mixture was cooled to 0° and adjusted to pH 2 by addition of 12N HCl. Water (200 mL) was added and the solution was washed with methylene chloride (3×50 mL). The combined organic layers were washed with brine, dried (magnesium sulfate) and evaporated to provide nonaethylene glycol methyl tosyl ether as a colorless oil (2.7 g); 1H-NMR (DMSO-d6)δ: 7.85 and 7.55 (2d, 4, C6H4), 4.18 (m, 2, CH2OTos), 3.7–3.45 (m 34, 17 CH2), 3.2 (s, 3, OCH3) 2.40 (s, 3, CH3). the mixture was cooled to 0° the solution was washed with methylene chloride (3×50 mL) The combined organic layers were washed with brine dried (magnesium sulfate) evaporated

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

Procedure: To a solution of nonaethylene glycol monomethyl ether (2.0 g. 4.7 mmol) in pyridine (15 mL) at 0° C. was added toluenesulfonyl chloride (1.35 g). After stiring at room temperature overnight, the mixture was cooled to 0° and adjusted to pH 2 by addition of 12N HCl. Water (200 mL) was added and the solution was washed with methylene chloride (3×50 mL). The combined organic layers were washed with brine, dried (magnesium sulfate) and evaporated to provide nonaethylene glycol methyl tosyl ether as a colorless oil (2.7 g); 1H-NMR (DMSO-d6)δ: 7.85 and 7.55 (2d, 4, C6H4), 4.18 (m, 2, CH2OTos), 3.7–3.45 (m 34, 17 CH2), 3.2 (s, 3, OCH3) 2.40 (s, 3, CH3). the mixture was cooled to 0° the solution was washed with methylene chloride (3×50 mL) The combined organic layers were washed with brine dried (magnesium sulfate) evaporated

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

Procedure: A solution of nonaethylene glycol benzyl methyl ether (10 g, 19.3 mmol) in ethanol (200 mL) was shaken with 10% palladium on activated charcal (Aldrich, 1.0 g) under hydrogen (50 psi) on a Parr apparatus for 3 h. The catalyst was filtered off (Celite), and the filtrate was concentrated in vacuo and dried by evaporation of toluene to provide nonaethylene glycol monomethyl ether as an oil (8.17 g, 99%), 1H-NMR (DMSO-d6) δ: 4.56 (t, 1 OH), 3.60–3.35 (m, 36, 18 OCH2), 3.22 (s, 3, CH3). The catalyst was filtered off (Celite) the filtrate was concentrated in vacuo dried by evaporation of toluene