Water → 2-(2-(2-Methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate
Reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][OH:11].[OH-].[Na+].[C:14]1(C)[C:15]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:17]=[CH:18][CH:19]=1.O.O1CCC[CH2:27]1>>[CH3:27][C:18]1[CH:19]=[CH:14][C:15]([S:20]([O:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])(=[O:21])=[O:22])=[CH:16][CH:17]=1Participants
Conditions
- Temperature
- 20 °C
Procedure
A solution of triethylene glycol monomethyl ether (300 g) in tetrahydrofuran (550 mL) was added dropwise over 105 minutes to a stirred aqueous sodium hydroxide solution (2M, 1.28 L) at 0–5° C. A solution of p toluenesulphonyl chloride (383 g) in tetrahydrofuran (600 mL) was then added to the reaction mixture over 150 minutes, maintaining the temperature at 0–9° C. The reaction mixture was stirred at 0–5° C. for a further 2 hours and then allowed to warm to 20° C. and stirred for 16 hours. Additional aqueous sodium hydroxide solution (2M, 90 mL) was then added slowly to the reaction mixture and stirring was continued for a further 1 hour. Water (1 L) was added to the reaction mixture which was then extracted with toluene (2×1.8 L). The combined organic extracts were washed with water (3×1.8 L) and then concentrated in vacuo to give the title compound as a colourless oil (448 g). GC retention time 11.2 mins
Workup
- temperaturemaintaining the temperature at 0–9° C
- stirringstirred for 16 hours
- stirringstirring
- waitwas continued for a further 1 hour
- extractionwas then extracted with toluene (2×1.8 L)
- washThe combined organic extracts were washed with water (3×1.8 L)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-2fc21741291d43ebb6d389a20f2d78d1
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07217409B2
Reaction notes
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