Diphenyl sulfoxide → HCID 14738647, compound

HRID 1757601Notes

Reaction equation

HRID 1757601 reaction equation
[C:1]1([S:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:15]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[F:30][P-:31]([F:36])([F:35])([F:34])([F:33])[F:32].[K+]>O>[F:30][P-:31]([F:36])([F:35])([F:34])([F:33])[F:32].[CH2:15]([O:23][C:24]1[CH:25]=[CH:26][C:27]([S+:7]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:28][CH:29]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 13679Diphenyl sulfoxide2×HCID 74558Octyl phenyl ether2×HCID 23688904Potassium hexafluorophosphate

Product 1

HCID 14738647HCID 14738647, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
42 °C

Procedure

A mixture of 12.12 grams (0.06 mole) of diphenylsulfoxide, 10.3 gram of octylphenyl ether and 20 ml of PP/MSA resulted in an exothermic reaction. The temperature of the mixture increased to 42° C. After the exotherm had subsided, the temperature was raised to 50° C. and maintained at that temperature for 1 hour with stirring. There was obtained a complex reaction product of diphenylsulfoxide and octylphenyl ether. The mixture was then poured into 200 ml of water. A clear yellow solution was obtained. There was added to the solution, 9.5 grams of potassium hexafluorophosphate. A yellow oil precipitated from the solutionwhich solidified to a white crystalline solid upon standing. The mixture was warmed slightly to 40° C. and stirred. There was obtained a quantitative yield of crude product. The product was recovered by filtering and washed twice with water followed by petroleum ether. The crude product was further purified by recrystallization from absolute ethanol. (4-octyloxyphenyl)diphenylsulfonium hexafluorophosphate was obtained at a 74% yield. It had a melting point of 94°-95° C.

Workup

  1. customresulted in an exothermic reaction
  2. temperaturethe temperature was raised to 50° C.
  3. temperaturemaintained at that temperature for 1 hour
  4. customThere was obtained
  5. customA clear yellow solution was obtained
  6. customA yellow oil precipitated from the solutionwhich solidified to a white crystalline solid
  7. temperatureThe mixture was warmed slightly to 40° C.
  8. stirringstirred
  9. customThere was obtained a quantitative yield of crude product
  10. customThe product was recovered
  11. filtrationby filtering
  12. washwashed twice with water
  13. customThe crude product was further purified by recrystallization from absolute ethanol

Sources & evidence

ORD record
ord-3dc3b72fc9224d9298a32ae16b9813f6
Source dataset
uspto-grants-1995_08
Patent number
US05446172

Reaction notes

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