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

HRID 1086952Notes

Reaction equation

HRID 1086952 reaction equation
[OH-].[Na+].[C:3]1(C)C=CC=CC=1.COS([O-])(=O)=O.[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>O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:16]([O:23][C:24]1[CH:32]=[C:31]2[C:27]([CH:28]=[CH:29][N:30]2[CH3:3])=[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

To 125 g of caustic soda in pellets in 125 ml water are added 300 ml toluene, 50 ml methylsulphate and 7.36 g tetrabutylammonium hydrogensulphate, then, with stirring, 0.33 mole (73.6 g) 6-benzyloxyindole. Stirring is maintained for 15 minutes after the end of the evolution of heat. The reaction medium is diluted with two 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 the aqueous phase
  5. extractionis extracted with toluene
  6. washAfter washing the organic phases with water
  7. customdrying them

Sources & evidence

ORD record
ord-90206bd4933f4f4ca87e8ae8907afb2c
Source dataset
uspto-grants-1991_07
Patent number
US05034015

Reaction notes

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