(3-Bromo-2-methylphenyl)methanol → 3-Bromo-2-methylbenzaldehyde

HRID 2386577Notes

Reaction equation

HRID 2386577 reaction equation
[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([CH2:8][OH:9])[CH:5]=[CH:6][CH:7]=1>C(Cl)Cl.[O-2].[Mn+2]>[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH:8]=[O:9]

Participants

4

Reactant 1

HCID 10035697(3-Bromo-2-methylphenyl)methanol

Product 1

HCID 104427433-Bromo-2-methylbenzaldehydeYield 93%

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

(3-bromo-2-methylphenyl)methanol was oxidized as follows: The alcohol (15 mmol) was dissolved in methylene chloride (30 mL). 10 equivalents of activated manganese oxide (IV) was added and the mixture stirred at room temperature for 24 hours. The mixture was filtered through a bed of celite and the solvent removed in-vacuo to leave yellow solid. Product was used crude in next step without further purification. The yield was 93%. 1H NMR (Varian 300 MHz, CDCl3, shifts relative to the solvent peak at 7.24 ppm) δ 9.8 (s, 1H) 8.1 (d, 1H) 7.7 (d, 1H), 7.2 (t, 1H), 2.4 (s, 3H).

Workup

  1. filtrationThe mixture was filtered through a bed of celite
  2. customthe solvent removed in-vacuo
  3. customto leave yellow solid
  4. customwithout further purification

Sources & evidence

ORD record
ord-2887bb3fb2e4476b8e86abc8be0eda5a
Source dataset
uspto-grants-2012_09
Patent number
US08268822B2

Reaction notes

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