Methanol → 2,6-Dichloro-4-methoxybenzaldehyde

HRID 1180350Notes

Reaction equation

HRID 1180350 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([Cl:10])[C:3]=1[CH2:11][OH:12].CO>C1C=CC=CC=1.O=[Mn]=O>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([Cl:10])[C:3]=1[CH:11]=[O:12]

Participants

5

Reactant 2

HCID 887MethanolHCID 14484725(2,6-Dichloro-4-methoxyphenyl)methanol

Product 1

HCID 147717592,6-Dichloro-4-methoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 241BenzeneSolvent

Procedure

A suspension of (2,6-dichloro-4-methoxy-phenyl)-methanol (5.69 g, 27.49 mmol) and MnO2 (15 g) in benzene (100 mL) was stirred at reflux, utilizing a Dean-Stark trap, overnight. The suspension was cooled to room temperature, filtered through Celite, and the solvent was removed by evaporation to yield 4.69 g (83%) of crude white solid. An analytical sample was obtained by recrystallization from methanol to yield white needle crystals: mp 104-106° C.; 1H NMR (DMSO-d6): δ 3.90 (3H, s), 7.21 (2H, s), 10.29 (1H, s); MS (EI) m/z 204/206/218 (M+−).

Workup

  1. temperatureat reflux
  2. customa Dean-Stark trap, overnight
  3. filtrationfiltered through Celite
  4. customthe solvent was removed by evaporation
  5. customto yield 4.69 g (83%) of crude white solid
  6. customto yield white needle crystals

Sources & evidence

ORD record
ord-e8476fd2320b475e8d05b5ab7e1fddcd
Source dataset
uspto-grants-2007_10
Patent number
US07279600B2

Reaction notes

Loading…