Diphenyl sulfide → 1,1'-Sulfanediylbis(4-tert-butylbenzene)

HRID 1462313Notes

Reaction equation

HRID 1462313 reaction equation
[C:1]1([S:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14](Cl)([CH3:17])([CH3:16])[CH3:15].[Al+3].[Cl-].[Cl-].[Cl-]>C(=S)=S>[C:14]([C:11]1[CH:10]=[CH:9][C:8]([S:7][C:1]2[CH:2]=[CH:3][C:4]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:5][CH:6]=2)=[CH:13][CH:12]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 8766Diphenyl sulfideHCID 10486tert-BUTYL CHLORIDEHCID 6451240Aluminum(III) Chloride

Product 1

HCID 133451781,1'-Sulfanediylbis(4-tert-butylbenzene)Yield 97.3%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a mixture of 93 g of phenyl sulfide, 92.5 g of t-butyl chloride and 200 mL of CS2 cooled in an ice bath, 133 g of AlCl3 was added over a period of 1 hour. Following complete addition, the mixture was allowed to warm slowly to room temperature and stirred overnight. The mixture was subjected to decomposition with ice, extraction with ether and washing of the ether solution successively with water, 5% NaHCO3, water and saturated NaCl solution and gave after evaporation of dried (MgSO4) extracts, a solid which upon crystallization from methanol gave 145 g (97%) of the sulfide as white crystals, m.p. 83-84; 'H NMR (CDCl3) δ 1.32 (s, 18H, CH3), 7.35 (s, 8H, aryl).

Workup

  1. temperaturecooled in an ice bath
  2. additionaddition
  3. extractionThe mixture was subjected to decomposition with ice, extraction with ether
  4. washwashing of the ether solution successively with water, 5% NaHCO3, water and saturated NaCl solution
  5. customgave
  6. customafter evaporation
  7. dry with materialof dried (MgSO4)
  8. customa solid which upon crystallization from methanol

Sources & evidence

ORD record
ord-9a353e46e27e42b885964e3d89cc965f
Source dataset
uspto-grants-1984_07
Patent number
US04460501

Reaction notes

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