Pyridine → 2-(2-(2-Methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate

HRID 891238Notes

Reaction equation

HRID 891238 reaction equation
[C:1]1(C)[C:2]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[CH3:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][OH:22].N1C=CC=C[CH:24]=1>>[S:7]([O:22][CH2:21][CH2:20][O:19][CH2:18][CH2:17][O:16][CH2:15][CH2:14][O:13][CH3:12])([C:2]1[CH:1]=[CH:6][C:5]([CH3:24])=[CH:4][CH:3]=1)(=[O:8])=[O:9]

Participants

4

Reactant 3

HCID 1049PyridineHCID 8178Triethylene glycol monomethyl etherHCID 8623o-Toluenesulfonyl chloride

Product 1

HCID 99488982-(2-(2-Methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate

Procedure

A solution of toluene sulfonyl chloride (Aldrich, 38 g) and triethylene glycol monomethyl ether (Aldrich, 16.4 g) in dry pyridine (150 ml) was stirred at 0° C. (icebath) for 4 h, followed by 18 h at ambient temperature. The solution was then poured onto ice water (500 ml) and extracted with diethyl ether extracts were combined, washed with hydrochloric acid (3 N) and water, dried (sodium sulfate), and concentrated to provide triethylene glycol methyl tosyl ether as a colorless oil (20.0 g, 62% based on glycol), 1H-NMR (CDCl3) δ: 7.75 (d, J=8.0 Hz, 2, 2 phenyl CH), 7.30 (d, J=8.1 Hz, 2, 2 phenyl CH), 4.11 (t, J=4.8 Hz, 2, CH2OS), 3.65–3.41 (m, 10, 5 CH2O), 3.32 (s, 3, CH3O) and 2.40 (s, 3, benzylic CH3).

Workup

  1. additionThe solution was then poured onto ice water (500 ml)
  2. extractionextracted with diethyl ether extracts
  3. washwashed with hydrochloric acid (3 N) and water
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6ea5f308418b47fa9357dba61e2190ab
Source dataset
uspto-grants-2006_02
Patent number
US07002012B2

Reaction notes

Loading…