p-Toluenesulfonate → HCID 22342188, compound

HRID 1638968Notes

Reaction equation

HRID 1638968 reaction equation
[C:1]1([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(C1C=CC(C)=CC=1)(O[IH:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=O)(=O)=O.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[F:56][Sb-:57]([F:62])([F:61])([F:60])([F:59])[F:58].[Na+]>CC(C)=O.C(O)(=O)C>[F:56][Sb-:57]([F:62])([F:61])([F:60])([F:59])[F:58].[CH2:8]([O:7][C:1]1[CH:6]=[CH:5][C:4]([I+:30][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:3][CH:2]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

7

Reactant 4

HCID 85570p-ToluenesulfonateHCID 292601Octadecyl phenyl ether2×HCID 16689647Sodium hexafluoroantimonateHCID 178427798HCID 178427798, compound

Product 1

HCID 22342188HCID 22342188, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 180AcetoneSolvent

Conditions

Temperature
40 °C

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.

Workup

  1. customa quantitative yield was obtained
  2. dissolutiondissolved in 200 ml dicholoromethane
  3. filtrationthe reaction mixture was filtered
  4. customthen triturated with ether
  5. customA product, (4-octadecyloxyphenyl)phenyliodonium tosylate crystallized from solution
  6. filtrationwas recovered by filtration
  7. customThere was obtained 340 grams (94.4% yield)
  8. stirringThe reaction mixture was stirred for 1 hour
  9. filtrationthe solution filtered
  10. customto remove the sodium tosylate
  11. customThe main filtrate was triturated with water

Sources & evidence

ORD record
ord-6faab0f5d1174b7d889f18ffe5e9cf08
Source dataset
uspto-grants-1989_11
Patent number
US04882201

Reaction notes

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