(2-Amino-4-chlorophenyl)methanol → 2-Amino-4-chlorobenzaldehyde

HRID 2364582Notes

Reaction equation

HRID 2364582 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][OH:10]>C(Cl)Cl.[O-2].[Mn+4].[O-2]>[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]=[O:10]

Participants

4

Reactant 1

HCID 4134900(2-Amino-4-chlorophenyl)methanol

Product 1

HCID 112521382-Amino-4-chlorobenzaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

In a 2 L 3-neck round bottom flask, the stirred solution of (2-amino-4-chlorophenyl)methanol 2 (32 g, 203.82 mmol) in DCM (765 mL), manganese (IV) oxide (150 g, 1.724 mol) was added at rt. The resulting reaction mixture was stirred at rt under argon atmosphere for 40 h. On completion of reaction the reaction mixture was filtered through CELITE™ pad and solid residue was washed thoroughly with DCM (1000 mL). The combined filtrate was concentrated under reduced pressure to give 2-amino-4-chlorobenzaldehyde as orange solid. Yield: 24 g (76.2%).

Workup

  1. customThe resulting reaction mixture
  2. customOn completion of reaction the reaction mixture
  3. filtrationwas filtered through CELITE™ pad and solid residue
  4. washwas washed thoroughly with DCM (1000 mL)
  5. concentrationThe combined filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8fcbc6fed30b49cea257f1d621cdb7f6
Source dataset
uspto-grants-2014_04
Patent number
US08691986B2

Reaction notes

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