Reaction #1340571

Reaction equation

2-chloroethyl vinylether

Sodium hydroxide

bis(4-hydroxyphenyl)phenylsulfonium triflate

DMSO

diethyl ether

ether

→

bis(4-vinyloxyethyloxyphenyl)phenylsulfonium triflate

Yield 61.5%

Solvents

DI water

Conditions

Workup

1. 1
   OtherA 3-neck-round bottom flask was fitted with a condenser, an addition funnel
2. 2
   TemperatureThe temperature was then increased to 80° C.
3. 3
   Temperatureto cool down to room temperature
4. 4
   Otherto form three layers
5. 5
   Washto wash the ether solution 3 times
6. 6
   OtherAn oily layer was collected
7. 7
   Concentrationconcentrated to dryness

Procedure

A 3-neck-round bottom flask was fitted with a condenser, an addition funnel, nitrogen source, and a magnetic bar. Sodium hydroxide (8.64 g, 0.216 mol), bis(4-hydroxyphenyl)phenylsulfonium triflate (16 g, 0.036 mol) and DMSO (90 ml) were added to a round bottom flask under N2. The mixture was heated to 60° C. for 1 hour. 2-chloroethyl vinylether (23 g, 0.216 mol) was added dropwise to the mixture via the addition funnel. The temperature was then increased to 80° C. and the reaction was held at that temperature for 5 hours. The reaction mixture was then allowed to cool down to room temperature. Thereafter, the reaction mixture was poured into diethyl ether to form three layers: aqueous, ether, and an oil. DI water was used to wash the ether solution 3 times. An oily layer was collected and concentrated to dryness. 12.9 g (61.5%) of bis(4-vinyloxyethyloxyphenyl)phenylsulfonium triflate was obtained. The structure was confirmed using 1H and 19F NMR.

Source