Hydrochloric Acid → m-PEG10-Tos

HRID 276809Notes

Reaction equation

HRID 276809 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][OH:29].[C:30]1(C)[C:31]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:33]=[CH:34][CH:35]=1.Cl.O.N1C=CC=C[CH:44]=1>>[S:36]([O:29][CH2:28][CH2:27][O:26][CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])([C:31]1[CH:30]=[CH:35][C:34]([CH3:44])=[CH:33][CH:32]=1)(=[O:37])=[O:38]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 1049PyridineHCID 8623o-Toluenesulfonyl chlorideHCID 11339376Nonaethylene Glycol Monomethyl Ether

Product 1

HCID 123132076m-PEG10-Tos

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).

Workup

  1. customAfter stiring at room temperature
  2. temperaturethe mixture was cooled to 0°
  3. washthe solution was washed with methylene chloride (3×50 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated

Sources & evidence

ORD record
ord-bf7b16c469054beaaa793c5652441e2f
Source dataset
uspto-grants-2002_03
Patent number
US06355646B1

Reaction notes

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