Cyclohexane → Indole-4-carboxaldehyde

HRID 2100342Notes

Reaction equation

HRID 2100342 reaction equation
[OH:1][CH2:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2.C1CCCCC1>ClCCl.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2)=[O:1]

Participants

5

Reactant 2

HCID 8078CyclohexaneHCID 27734571H-indol-4-ylmethanol

Product 1

HCID 333703Indole-4-carboxaldehydeYield 86.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Manganese dioxide (MnO2) is added slowly with stirring to a solution of 74 g of 4-hydroxymethylindole (2) in 3 litres of dichloromethane, and the mixture is subsequently stirred at room temperature for 72 hours. The reaction mixture is subsequently filtered through kieselguhr, and the filtrate is evaporated. The crystalline residue obtained is stirred with cyclohexane and filtered under reduced pressure. Drying gives 63 g (86% of theory) of crystalline 4-formylindole (3).

Workup

  1. filtrationThe reaction mixture is subsequently filtered through kieselguhr
  2. customthe filtrate is evaporated
  3. customThe crystalline residue obtained
  4. filtrationfiltered under reduced pressure
  5. customDrying

Sources & evidence

ORD record
ord-9dd8ac0bc87e49fdb673db4e2fc4242b
Source dataset
uspto-grants-2009_08
Patent number
US07572796B2

Reaction notes

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