4-Toluenesulfonyl chloride → 2-(2-(2-Hydroxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate
Reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:12]([OH:21])[CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][OH:20]>N1C=CC=CC=1>[S:7]([O:21][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][OH:20])([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
p-Toluenesulfonyl chloride (17.1 g) was added portionwise to triethylene glycol (15 g) in pyridine (600 ml) at 0° C. The solution was allowed to warm to room temperature and stirring continued for 16 h. The solvent was removed under reduced pressure to approximately 50 ml and the residue diluted with hydrochloric acid (100 ml, 3M), extracted with dichloromethane (3×100 ml), washed with brine (150 ml), dried (Na2SO4), and the solvent removed under reduced pressure. The resulting pale orange oil was purified by flash chromatography (ethyl acetate) to give triethylene glycol mono tosylate from the most polar fractions as a clear oil (6.94 g, 23%). 1H nmr (CDCl3) δ2.44 (s, 3H), 2.56 (br s, 1H OH), 3.56-3.73 (m, 10H), 4.16 (m, 2H), 7.38 and 7.78 (AB quartet, 2H each); 13C nmr (CDCl3) δ21.33, 42.52, 61.25, 68.31, 69.00, 69.86, 70.36, 72.25, 127.64, 129.63, 144.71; m/z (CI) 305 (M+H)+.
Workup
- customThe solvent was removed under reduced pressure to approximately 50 ml
- additionthe residue diluted with hydrochloric acid (100 ml, 3M)
- extractionextracted with dichloromethane (3×100 ml)
- washwashed with brine (150 ml)
- dry with materialdried (Na2SO4)
- customthe solvent removed under reduced pressure
- customThe resulting pale orange oil was purified by flash chromatography (ethyl acetate)
Sources & evidence
- ORD record
- ord-08a0834574a146ffa35fc8fca8b4a933
- Source dataset
- uspto-grants-2002_07
- Patent number
- US06417009B1
Reaction notes
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