O-Xylene → 1,2-Bis(propylsulfanyl)benzene

HRID 2231608Notes

Reaction equation

HRID 2231608 reaction equation
[CH2:1]([S:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:11])[CH2:2][CH3:3].C1(C)C(C)=CC=CC=1.[CH2:20]([SH:23])[CH2:21][CH3:22]>ClC1C=CC=CC=1Cl.C1(C)C=CC=CC=1>[CH2:1]([S:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:11])[CH2:2][CH3:3].[CH2:1]([S:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:23][CH2:20][CH2:21][CH3:22])[CH2:2][CH3:3]

Participants

7

Reactant 3

HCID 7237O-XyleneHCID 7848Propyl mercaptanHCID 118702o-Chlorophenyl propyl sulfide

Product 2

HCID 118702o-Chlorophenyl propyl sulfideHCID 144911741,2-Bis(propylsulfanyl)benzeneYield 56.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 72391,2-DichlorobenzeneSolvent

Procedure

A solution of 215 g of 61.5 weight % of o-chlorophenyl propyl sulfide in o-dichlorobenzene (ODCB) was combined with 222.8 g of 85% potassium propyl mercaptide, 200 ml of xylene, 45 g of Carbowax®350, polyethyleneglycol (Union Carbide), and 20 ml of propyl mercaptan, and heated at reflux for 96 hours. The liquid temperature of the refluxing mixture, initially at 137° C., rose to 168° after 64 hours, and to 198° C. after 86 hours. The dark solution was cooled, diluted with 300 ml of toluene, and washed with water to remove inorganic salts. The organic phase was dried (MgSO4) and fractionally distilled to give 48.6 g of recovered o-chlorophenyl propyl sulfide and 129.6 g (56.4%) of ortho-bis-propylthiobenzene, b.p. 100°-105° C. (0.06 mmHg).

Workup

  1. temperatureheated
  2. temperatureat reflux for 96 hours
  3. waitto 198° C. after 86 hours
  4. temperatureThe dark solution was cooled
  5. washwashed with water
  6. customto remove inorganic salts
  7. dry with materialThe organic phase was dried (MgSO4)
  8. distillationfractionally distilled

Sources & evidence

ORD record
ord-9f0a4664f34e42a1a9e7202a5fb4ebce
Source dataset
uspto-grants-1988_11
Patent number
US04783285

Reaction notes

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