Reaction #927229

Reaction equation

acetoxystyrene

t-butyl acrylate

→

Hydroxystyrene

Solvents

toluene

Conditions

Workup

1. 1
   OtherThe reactor was purged with nitrogen
2. 2
   TemperatureThe solution was then cooled to room temperature
3. 3
   workup.ADDITIONdiluted with an additional 12 L of toluene, and 248 L of heptane:isopropyl alcohol (30:1)
4. 4
   workup.ADDITIONwas added
5. 5
   FiltrationThe precipitate was collected by vacuum filtration
6. 6
   Washwashed with 24 L heptane
7. 7
   OtherThe solid was recrystalized
8. 8
   workup.DISSOLUTIONby first dissolving it in 15 L acetone
9. 9
   workup.ADDITIONadding 300 L isopropyl alcohol:water (51:24 v/v)
10. 10
    FiltrationThe product was collected by vacuum filtration
11. 11
    Washrinsed with 30 L 1:1 isoproyl alcohol
12. 12
    Dryingwater, and then dried at 50-55° C. under vacuum to a constant weight

Procedure

A 22 L reactor was charged with 2.919 kg acetoxystyrene, 1.538 kg t-butyl acrylate, 231 g BPO and 6 L toluene. The reactor was purged with nitrogen, and the reaction solution was heated at 60° C. under a N2 atmosphere for 23 h. The solution was then cooled to room temperature, diluted with an additional 12 L of toluene, and 248 L of heptane:isopropyl alcohol (30:1) was added. The precipitate was collected by vacuum filtration, and washed with 24 L heptane. The solid was recrystalized by first dissolving it in 15 L acetone and then adding 300 L isopropyl alcohol:water (51:24 v/v). The product was collected by vacuum filtration, rinsed with 30 L 1:1 isoproyl alcohol:water, and then dried at 50-55° C. under vacuum to a constant weight.

Source