Toluene → 6-(Benzyloxy)-1-methyl-1H-indole

HRID 1198089Notes

Reaction equation

HRID 1198089 reaction equation
[C:1]1(C)C=CC=CC=1.COS([O-])(=O)=O.[OH-].[Na+].[CH2:16]([O:23][C:24]1[CH:32]=[C:31]2[C:27]([CH:28]=[CH:29][NH:30]2)=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:16]([O:23][C:24]1[CH:32]=[C:31]2[C:27]([CH:28]=[CH:29][N:30]2[CH3:1])=[CH:26][CH:25]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 2608046-(benzyloxy)-1H-indoleHCID 4694097Methyl sulfate(1-)

Product 1

HCID 123483846-(Benzyloxy)-1-methyl-1H-indole

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent2×

Procedure

300 ml of toluene, 50 ml of methylsulphate and 7.36 g of tetrabutylammonium hydrogen sulphate are added to 125 g of sodium hydroxide pellets in 125 ml of water, then, with stirring, 0.33 mole (73.6 g) of 6-benzyloxyindole. Stirring is maintained for 15 minutes after the end of the evolution of heat. The reaction medium is diluted with 2 volumes of water. After separation of the organic phase, the aqueous phase is extracted with toluene. After washing the organic phases with water and drying them, the desired product is obtained by evaporation. It melts at 79° C.

Workup

  1. stirringStirring
  2. temperatureis maintained for 15 minutes after the end of the evolution
  3. temperatureof heat
  4. customAfter separation of the organic phase
  5. extractionthe aqueous phase is extracted with toluene
  6. washAfter washing the organic phases with water
  7. customdrying them

Sources & evidence

ORD record
ord-8c508b7f896f46be987e399e9e53673a
Source dataset
uspto-grants-1994_01
Patent number
US05279620

Reaction notes

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