Potassium Iodide → (4-Hydroxy-3,5-dimethylphenyl)(diphenyl)sulfanium iodide

HRID 917258Notes

Reaction equation

HRID 917258 reaction equation
[C:1]1([OH:9])[C:2]([CH3:8])=[CH:3][CH:4]=[CH:5][C:6]=1[CH3:7].[C:10]1([S:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.CS(O)(=O)=O.[I-:43].[K+]>O>[I-:43].[CH3:8][C:2]1[CH:3]=[C:4]([S+:16]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:6]([CH3:7])[C:1]=1[OH:9]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 113352,6-DimethylphenolHCID 13679Diphenyl sulfoxideHCID 86584057Phosphorus Pentoxide-Methanesulfonic Acid

Product 1

HCID 71360004(4-Hydroxy-3,5-dimethylphenyl)(diphenyl)sulfanium iodide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 36 g of 2,6-xylenol and 60 g of diphenyl sulfoxide was added 300 mL of a solution consisting of diphosphorous pentoxide/methanesulfonic acid=1/10. The resultant reaction mixture was reacted at 40° C. for 4 hours and then poured on ice. This aqueous solution was washed with ethyl acetate. To the aqueous phase was added a solution prepared by dissolving 200 g of potassium iodide in water. The particles precipitated were taken out by filtration and washed with acetone. As a result, 3,5-dimethyl-4-hydroxyphenyldiphenylsulfonium iodide was obtained in an amount of 80 g. To 7.1 g of the 3,5-dimethyl-4-hydroxyphenyldiphenylsulfonium iodide obtained were added 300 mL of chloroform and 2.0 g of triethylamine. To this solution was dropwise added 10 g of nonafluorobutanesulfonic anhydride over 30 minutes with cooling with ice. After the resultant reaction mixture was reacted at room temperature for 1 hour, water was added thereto. The organic phase was washed with 5% aqueous NaOH solution and subsequently with water and then concentrated to obtain a crude reaction product, which was recrystallized from ethyl acetate/dilsopropyl ether. As a result, acid generator (Bb-1) was obtained in an amount of 10.0 g.

Workup

  1. customThe resultant reaction mixture
  2. customwas reacted at 40° C. for 4 hours
  3. additionpoured on ice
  4. washThis aqueous solution was washed with ethyl acetate
  5. additionTo the aqueous phase was added a solution
  6. customprepared
  7. customThe particles precipitated
  8. filtrationwere taken out by filtration
  9. washwashed with acetone

Sources & evidence

ORD record
ord-92b3a18963c74c67a5bfced3d6488121
Source dataset
uspto-grants-2007_09
Patent number
US07273690B2

Reaction notes

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