Dichloromethane → 1-Benzyl-2-methylimidazole-4-carboxaldehyde

HRID 638221Notes

Reaction equation

HRID 638221 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([CH2:13][OH:14])[N:10]=[C:9]1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)Cl.CCCCCC>C(OCC)C.[O-2].[O-2].[Mn+4]>[CH2:1]([N:8]1[CH:12]=[C:11]([CH:13]=[O:14])[N:10]=[C:9]1[CH3:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 8058HexaneHCID 136062411-Benzyl-4-hydroxymethyl-2-methylimidazole

Product 1

HCID 136062421-Benzyl-2-methylimidazole-4-carboxaldehydeYield 81%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

A slurry of 9.0 g (0.446 mole) of 1-benzyl-4-hydroxymethyl-2-methylimidazole, 750 ml of methylene chloride and 50.0 g (0.575 mole) of manganese dioxide was stirred at room temperature for two hours. It was then filtered, the filter cake washed with methylene chloride and the combined filtrate and wash solutions evaporated under reduced pressure to give an oil. The oil was taken up in 100 ml of diethyl ether, 100 ml of hexane added and the solution seeded with a few crystals of the title compound. Concentration of the solution under a nitrogen sweep with periodic replacement of hexane afforded a crystalline product which was isolated by filtration: 7.2 g, 81% yield; m.p. 57°-60° C.

Workup

  1. filtrationIt was then filtered
  2. washthe filter cake washed with methylene chloride
  3. washthe combined filtrate and wash solutions
  4. customevaporated under reduced pressure
  5. customto give an oil

Sources & evidence

ORD record
ord-5e0e962c5a0b429997ba52661c2e224f
Source dataset
uspto-grants-1985_12
Patent number
US04560690

Reaction notes

Loading…