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

HRID 707218

Reaction equation

HRID 707218 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)Cl.[O-2].[O-2].[Mn+4]>[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 6212ChloroformSolvent

Procedure

(2-amino-4-chlorophenyl)methanol (10.08 g, 64.0 mmol) was suspended in chloroform (250 mL) and treated with manganese dioxide (15.87 g, 183 mmol). The mixture was stirred vigorously and heated at reflux. The oxidation was followed by TLC and found to be complete after 1 hour. The suspension was filtered through a pad of CELITE™ and evaporated to dryness under reduced pressure. Further drying under high vacuum gave a dark red solid which was used in the next step without further purification.

Workup

  1. temperatureheated
  2. temperatureat reflux
  3. filtrationThe suspension was filtered through a pad of CELITE™
  4. customevaporated to dryness under reduced pressure
  5. customFurther drying under high vacuum
  6. customgave a dark red solid which
  7. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-2cf16fb38d554c9fa404efcf50bdba68
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Linked notes

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