4-Methylbenzyl chloride → Sulfide, bis(4-methylbenzyl)-

HRID 1886126Notes

Reaction equation

HRID 1886126 reaction equation
O.[S-2:2].[Na+].[Na+].[CH3:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10]Cl)=[CH:8][CH:7]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][S:2][CH2:5][C:6]2[CH:13]=[CH:12][C:9]([CH3:10])=[CH:8][CH:7]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 77224-Methylbenzyl chlorideHCID 19906495Sodium sulfide monohydrate

Product 1

HCID 139416Sulfide, bis(4-methylbenzyl)-Yield 95%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

A solution of 269.0 g (1.12 mol) of sodium sulfide hydrate and 12.0 g of tetrabutylammonium hydrogen sulfate (phase transfer catalyst) in 300 ml of water is introduced into a reaction vessel provided with a stirrer and thermometer. 212.6 g (1.52 mol) of 4-methylbenzyl chloride are added dropwise at below 40° C. in the course of 30 minutes (min), while stirring intensively. The reaction mixture is stirred at room temperature (RT) for 4 1/2 hours (h) and then at 50°-60° C. for 1/2 h. The reaction mixture is cooled to 0°-5° C. and kept at this temperature for 1/2 h. The reaction mixture is filtered and the residue is dissolved in about 2 liters of ethyl acetate. The organic phase is extracted twice by shaking with deionized water (pH ~6) and dried over MgSO4. The ethyl acetate is removed on a rotary evaporator. The residue is dried overnight at RT under a high vacuum. 174.8 g (95% of theory) of di-(p-methylbenzyl) sulfide are obtained as slightly yellowish white crystals having a melting point of 74°-76° C.

Workup

  1. customprovided with a stirrer
  2. stirringThe reaction mixture is stirred at room temperature (RT) for 4 1/2 hours (h)
  3. temperatureThe reaction mixture is cooled to 0°-5° C.
  4. waitkept at this temperature for 1/2 h
  5. filtrationThe reaction mixture is filtered
  6. dissolutionthe residue is dissolved in about 2 liters of ethyl acetate
  7. extractionThe organic phase is extracted twice
  8. stirringby shaking with deionized water (pH ~6)
  9. dry with materialdried over MgSO4
  10. customThe ethyl acetate is removed on a rotary evaporator
  11. customThe residue is dried overnight at RT under a high vacuum

Sources & evidence

ORD record
ord-5217aee23ef546738b09ca0408ec808b
Source dataset
uspto-grants-1992_09
Patent number
US05149767

Reaction notes

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