Sulfuric Acid → Allyl tritylsulfide

HRID 1085993Notes

Reaction equation

HRID 1085993 reaction equation
[CH2:1]([SH:4])[CH:2]=[CH2:3].[C:5](O)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.S(=O)(=O)(O)O>C(O)(=O)C>[CH2:1]([S:4][C:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6457TriphenylcarbinolHCID 13367Allyl Mercaptan

Product 1

HCID 637326Allyl tritylsulfide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

48 ml of allylmercaptan and 129.6 g of trityl alcohol were suspended in 500 ml of acetic acid and 2.0 ml of concentrated sulfuric acid was dropwise added thereto at room temperature with stirring. Then, the mixture was further stirred for one hour under the same conditions as above, and the precipitates were recovered therefrom by filtration, washed with 200 ml of methanol and then thoroughly washed with water. The resulting colorless powder was dissolved in benzene, washed with an aqueous 5% sodium hydrogen carbonate solution and then with water, and dried over anhydrous magnesium sulfate, and the solvent was removed therefrom by distillation under reduced pressure. The residue was treated with a small amount of methanol to obtain 130 g of allyl tritylsulfide (melting point: 99°-101° C.).

Workup

  1. stirringThen, the mixture was further stirred for one hour under the same conditions as above, and the precipitates
  2. customwere recovered
  3. filtrationby filtration
  4. washwashed with 200 ml of methanol
  5. washthoroughly washed with water
  6. dissolutionThe resulting colorless powder was dissolved in benzene
  7. washwashed with an aqueous 5% sodium hydrogen carbonate solution
  8. dry with materialwith water, and dried over anhydrous magnesium sulfate
  9. customthe solvent was removed
  10. distillationby distillation under reduced pressure
  11. additionThe residue was treated with a small amount of methanol

Sources & evidence

ORD record
ord-8f83ed7069ff4b1887e0bf8221ad254e
Source dataset
uspto-grants-1991_04
Patent number
US05011975

Reaction notes

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