Hydrochloric Acid → Triphenylsulfanium iodide

HRID 986901

Reaction equation

HRID 986901 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.[Cl-].[Al+3].[Cl-].[Cl-].Cl.[I-:20].[NH4+]>C1C=CC=CC=1>[I-:20].[C:1]1([S+:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13679Diphenyl sulfoxideHCID 25487Ammonium iodideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 21881071Triphenylsulfanium iodideYield 145.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
70 °C

Procedure

50 g of diphenyl sulfoxide was dissolved in 800 ml of benzene and thereto, 200 g of aluminum chloride was added and refluxed for 24 hours. The reaction solution was gradually poured into 2 L of ice and thereto, 400 ml of concentrated hydrochloric acid was added and heated at 70° C. for 10 minutes. This aqueous solution was washed with 500 ml of ethyl acetate and filtered. Thus, a solution obtained by dissolving 200 g of ammonium iodide was added thereto. The powder precipitated was collected by filtration, washed with water, washed with ethyl acetate and then dried. Thus, 70 g of triphenylsulfonium iodide was obtained.

Workup

  1. temperaturerefluxed for 24 hours
  2. washThis aqueous solution was washed with 500 ml of ethyl acetate
  3. filtrationfiltered
  4. customThus, a solution obtained
  5. additionwas added
  6. customThe powder precipitated
  7. filtrationwas collected by filtration
  8. washwashed with water
  9. washwashed with ethyl acetate
  10. customdried

Sources & evidence

ORD record
ord-b2aaeedf751549a1988ec944197f078a
Source dataset
uspto-grants-2003_10
Patent number
US06630280B1

Linked notes

Loading…