Benzene → 1,3-Dithiolane, 2,2-diphenyl-

HRID 1763222Notes

Reaction equation

HRID 1763222 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([SH:18])[CH2:16][SH:17].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>O>[C:2]1([C:1]2([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[S:18][CH2:15][CH2:16][S:17]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 3102BenzophenoneHCID 6101p-Toluenesulfonic acidHCID 109021,2-Ethanedithiol

Product 1

HCID 227711,3-Dithiolane, 2,2-diphenyl-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution containing benzophenone (45.5 grams; 0.25 mole), 1,2-ethanedithiol (23.5 grams; 0.25 mole), and p-toluenesulfonic acid (1 gram) in 150 mls. of dry benzene was heated at reflux until no more water was azeotroped off. The remaining benzene was then evaporated and the residue was dissolved in diethyl ether. The ethereal solution was then washed with water, dried over anhydrous magnesium sulfate, filtered and evaporated to obtain 2,2-diphenyl-1,3-dithiolane, a white crystalline solid which melted at 104°-105° C. A different preparation of this same compound is described in Fasbender, Berichte 21, 1473-7, (1888), wherein the melting point is reported as 106° C.

Workup

  1. customwas azeotroped off
  2. customThe remaining benzene was then evaporated
  3. dissolutionthe residue was dissolved in diethyl ether
  4. washThe ethereal solution was then washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-679abf404feb46b29049315c2f1308f0
Source dataset
uspto-grants-1978_09
Patent number
US04111873

Reaction notes

Loading…