Reaction #2446100

Reaction equation

p-Hydroxystyrene

triethylamine

ethyl acetate

→

desired resin

p-(1-(Cyclohexylethoxy)ethoxy)styrene p-Hydroxystyrene

Solvents

propylene glycol monomethyl ether acetate

Conditions

Workup

1. 1
   Temperaturewith heating
2. 2
   workup.DISTILLATIONdehydrated by vacuum distillation
3. 3
   workup.ADDITIONTo this solution, 0.35 g of pyridinium p-toluenesulfonate and 22.4 g of cyclohexane ethanol were added
4. 4
   workup.ADDITIONfurther 17.5 g of t-butyl vinyl ether was added at a slow speed
5. 5
   OtherIn the resulting mixture, reaction
6. 6
   Washwashed with 150 ml each of distilled water for three times
7. 7
   workup.DISTILLATIONTherefrom, the solvent was distilled away
8. 8
   Concentrationthe residue was concentrated
9. 9
   workup.DISSOLUTIONThe thus obtained oil was dissolved in 100 ml of acetone
10. 10
    workup.ADDITIONpoured slowly into 2 liter of distilled water
11. 11
    OtherAs a result, a powdery matter separated out
12. 12
    FiltrationThis powdery matter was filtered off
13. 13
    Otherdried

Procedure

p-Hydroxystyrene (VP-8000, produced by Nippon Soda Co., Ltd.) in an amount of 70 g was dissolved in 320 g of propylene glycol monomethyl ether acetate (PGMEA) with heating, dehydrated by vacuum distillation, and then cooled to 25° C. To this solution, 0.35 g of pyridinium p-toluenesulfonate and 22.4 g of cyclohexane ethanol were added, and further 17.5 g of t-butyl vinyl ether was added at a slow speed. In the resulting mixture, reaction was run for 5 hours at 20° C. Thereafter, the reaction solution was admixed with 0.28 g of triethylamine and 320 ml of ethyl acetate, and washed with 150 ml each of distilled water for three times. Therefrom, the solvent was distilled away, and the residue was concentrated. The thus obtained oil was dissolved in 100 ml of acetone, and poured slowly into 2 liter of distilled water. As a result, a powdery matter separated out. This powdery matter was filtered off and dried to yield 54 g of the desired resin.

Source