Reaction #1726150

Reaction equation

octadecyl phenyl ether

phenyliodoso tosylate

octadecyl phenyl ether

tosylate

sodium hexafluoroantimonate

→

(4-octadecyloxyphenyl)phenyliodonium hexafluoroantimonate

Solvents

acetic acid

acetone

Conditions

Workup

1. 1
   Othera quantitative yield was obtained
2. 2
   workup.DISSOLUTIONdissolved in 200 ml dicholoromethane
3. 3
   Filtrationthe reaction mixture was filtered
4. 4
   Otherthen triturated with ether
5. 5
   OtherA product, (4-octadecyloxyphenyl)phenyliodonium tosylate crystallized from solution
6. 6
   Filtrationwas recovered by filtration
7. 7
   OtherThere was obtained 340 grams (94.4% yield)
8. 8
   workup.STIRRINGThe reaction mixture was stirred for 1 hour
9. 9
   Filtrationthe solution filtered
10. 10
    Otherto remove the sodium tosylate
11. 11
    OtherThe main filtrate was triturated with water

Procedure

In accordance with the procedure of Example 1, octadecyl phenyl ether was prepared and a quantitative yield was obtained. There was added 50 ml of glacial acetic acid to a mixture of 196 grams (0.5 mol) of phenyliodoso tosylate and 173 grams (0.5 mols) of octadecyl phenyl ether dissolved in 200 ml dicholoromethane. After 1 hour stirring at 40° C., the reaction mixture was filtered then triturated with ether. A product, (4-octadecyloxyphenyl)phenyliodonium tosylate crystallized from solution and was recovered by filtration. There was obtained 340 grams (94.4% yield). The entire amount of the tosylate salt was dissolved in 1000 ml of hot acetone and 125 grams of sodium hexafluoroantimonate was added. The reaction mixture was stirred for 1 hour and the solution filtered to remove the sodium tosylate. The main filtrate was triturated with water and a white crystalline product (4-octadecyloxyphenyl)phenyliodonium hexafluoroantimonate was obtained. Recrystallization from ethanol/water gave the pure iodonium salt having a melting point of 94° C. and an 83 % yield. The acute oral toxicity of this photoinitiator was found to be greater than 5 g/kg. No toxic effects were observed during the 14 day test period and all the test animals (rats) gained weight during the test period.

Source