Toluene → HCID 10658876, compound

HRID 863904Notes

Reaction equation

HRID 863904 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[OH-].[Na+].C1(C)C=CC=CC=1.[CH2:18]1[O:28][C:27]2[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][C:20]=2[O:19]1>O.C(Cl)Cl.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:23][C:22]2[CH:25]=[CH:26][C:27]3[O:28][CH2:18][O:19][C:20]=3[CH:21]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 78114-MethylbenzenethiolHCID 14798Sodium Hydroxide2×HCID 887131,3-Benzodioxole, 5-(chloromethyl)-

Product 1

HCID 10658876HCID 10658876, compound

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 28.5 g of p-thiocresol in 250 mL of water is added 8.8 g of sodium hydroxide. The solution is heated on a steam bath briefly with vigorous stirring and then cooled to room temperature. To this solution is added 250 of toluene, 39.7 g of a 50% by weight solution of 3,4-methylenedioxybenzyl chloride in methylene chloride and 3.3 g of tetrabutylammonium chloride. This solution is stirred at room temperature for one hour and then 4.4 g of sodium hydroxide is added. The resulting solution is stirred at room temperature overnight and then partitioned. The organic layer is washed with 1N sodium hydroxide, brine, and dried over sodium sulfate. The solvent is removed at reduced pressure and the residual brown oil is purified via column chromatography using hexane/chloroform (2:1). This affords 24 g of the desired product as a clear oil. MS(CI): m/z 259(MH+). Calcd for C15H14O2S: C=69.74, H=5.46, S=12.41 Found C=69.53, H=5.36, S=12.69

Workup

  1. temperatureThe solution is heated on a steam bath briefly
  2. stirringThis solution is stirred at room temperature for one hour
  3. stirringThe resulting solution is stirred at room temperature overnight
  4. custompartitioned
  5. washThe organic layer is washed with 1N sodium hydroxide, brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent is removed at reduced pressure
  8. customthe residual brown oil is purified via column chromatography

Sources & evidence

ORD record
ord-9a6839f3f23a413087a13e9da29ccd58
Source dataset
uspto-grants-1996_10
Patent number
US05561141

Reaction notes

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