(4-Chloro-3-methoxyphenyl)methanol → 4-Chloro-3-methoxybenzaldehyde

HRID 1437558Notes

Reaction equation

HRID 1437558 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[O:10][CH3:11]>C1C=CC=CC=1.O=[Mn]=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][C:3]=1[O:10][CH3:11]

Participants

4

Reactant 1

HCID 10910038(4-Chloro-3-methoxyphenyl)methanol

Product 1

HCID 129097254-Chloro-3-methoxybenzaldehydeYield 89.7%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 241BenzeneSolvent

Procedure

To a solution of (4-chloro-3-methoxyphenyl)methan-1-ol (5.08 g, 29.4 mmol) in benzene (120 mL) was added MnO2 (5.65 g, 65 mmol). The reaction mixture was refluxed for 17 hr, chilled, and filtered through Celite, washing the cake with CH2Cl2 (300 mL). The filtrate was concentrated in vacuo to give 4-chloro-3-methoxybenzaldehyde (4.5 g, 89%).

Workup

  1. temperatureThe reaction mixture was refluxed for 17 hr
  2. temperaturechilled
  3. filtrationfiltered through Celite
  4. washwashing the cake with CH2Cl2 (300 mL)
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-099f9034e3084784886292c9ed949b1f
Source dataset
uspto-grants-2009_11
Patent number
US07622474B2

Reaction notes

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