(3-Bromo-4-methylphenyl)methanol → 3-Bromo-4-methylbenzaldehyde

HRID 2386571Notes

Reaction equation

HRID 2386571 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[CH:5]=[CH:6][C:7]=1[CH3:8]>C(Cl)Cl.[O-2].[Mn+2]>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[CH3:8])[CH:9]=[O:10]

Participants

4

Reactant 1

HCID 12947381(3-Bromo-4-methylphenyl)methanol

Product 1

HCID 8167653-Bromo-4-methylbenzaldehydeYield 89%

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

(3-bromo-4-methylphenyl)methanol was oxidized as follows: To the primary alcohol (15 mmol) in methylene chloride (30 mL) was added 10 equivalents of activated manganese oxide (IV). The mixture was stirred at room temperature for 24 hours, the filtered through a bed of celite. Removal of the solvent left a yellow solid. Product was used crude in next step without further purification. The yield was 89%. 1H NMR (Varian 300 MHz CDCl3, shifts relative to the solvent peak at 7.24 ppm) δ 9.8 (s, 1H) 8.0 (s, 1H) 7.7 (d, 1H), 7.2 (d, 1H), 2.3 (s, 3H).

Workup

  1. filtrationthe filtered through a bed of celite
  2. customRemoval of the solvent
  3. waitleft a yellow solid
  4. customwithout further purification

Sources & evidence

ORD record
ord-7624707fdc3c4f5cac9e8f4207271fee
Source dataset
uspto-grants-2012_09
Patent number
US08268822B2

Reaction notes

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