2-t-Butyl-5-hydroxymethyl-1-nitrobenzene → 2-t-Butyl-5-formyl-1-nitrobenzene

HRID 1418180Notes

Reaction equation

HRID 1418180 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][OH:12])=[CH:7][C:6]=1[N+:13]([O-:15])=[O:14])([CH3:4])([CH3:3])[CH3:2]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[O:12])=[CH:7][C:6]=1[N+:13]([O-:15])=[O:14])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 193485812-t-Butyl-5-hydroxymethyl-1-nitrobenzene

Product 1

HCID 193486202-t-Butyl-5-formyl-1-nitrobenzeneYield 94.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

240 g of manganese dioxide were added to a solution of 30 g (0.14 mol) of 2-t-butyl-5-hydroxymethyl-l-nitrobenzene (prepared as described in Preparation 10) in 450 ml of chloroform, and the resulting mixture was stirred at room temperature for 1 hour. At the end of this time, the reaction mixture was filtered to remove manganese dioxide, and the filtrate was freed from the solvent by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 1:5 by volume mixture of ethyl acetate and hexane as the eluent, to give 27.4 g of the title compound.

Workup

  1. filtrationAt the end of this time, the reaction mixture was filtered
  2. customto remove manganese dioxide
  3. distillationthe filtrate was freed from the solvent by distillation under reduced pressure
  4. customThe resulting residue was purified by column chromatography through silica gel
  5. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-85e23811202e4a2f956323e53173db5d
Source dataset
uspto-grants-1999_03
Patent number
US05880147

Reaction notes

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