Reaktion #1946545

Reaktionsgleichung

HCl

tosyl chloride

triethylene glycol monomethyl ether

NaOH

→

triethylene glycol monomethyl ether monotosylate

Lösungsmittel

THF

THF

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn an oven dried 12 L three-necked roundbottom flask
2. 2
   Sonstigeequipped with a magnetic stir bar
3. 3
   workup.STIRRINGThe reaction mixture is stirred for an additional 1 h at O° C
4. 4
   Sonstigeto quench
5. 5
   Sonstigethe reaction (to pH 5-7)
6. 6
   SonstigeThe two-phase mixture is transferred to a 4 L separatory funnel
7. 7
   Sonstigethe organic layer removed
8. 8
   Extraktionthe aqueous layer extracted with t-butylmethyl ether (3×250 mL)
9. 9
   WaschenThe combined organic extracts are washed with brine (2×350 mL)
10. 10
    Trocknendried (MgSO4)
11. 11
    Sonstigeevaporated under reduced pressure
12. 12
    Sonstigeto afford Formula B, 1217.6 g (95%) as a light colored oil
13. 13
    SonstigeThis material is taken to the next step without further purification

Vorschrift

In an oven dried 12 L three-necked roundbottom flask, equipped with a magnetic stir bar and a 1000 mL pressure-equalizing dropping funnel, a solution of NaOH (440.0 g, 11.0 mol) is added to 1800 mL water and the mixture is cooled to approximately 0° C. A solution of triethylene glycol monomethyl ether, Formula A, (656.84 g, 4.0 mol) in THF (1000 mL) is added. The clear solution is stirred vigorously at 0° C. for 15 min and a solution of tosyl chloride (915.12, 4.8 mol) in THF (2.0 L) added dropwise over a 1 h period. The reaction mixture is stirred for an additional 1 h at O° C., and 10% HCl (5.0 L) is added to quench the reaction (to pH 5-7). The two-phase mixture is transferred to a 4 L separatory funnel the organic layer removed, and the aqueous layer extracted with t-butylmethyl ether (3×250 mL). The combined organic extracts are washed with brine (2×350 mL), dried (MgSO4), and evaporated under reduced pressure to afford Formula B, 1217.6 g (95%) as a light colored oil. This material is taken to the next step without further purification.

Quelle