2-Amino-5-chlorobenzyl alcohol → 2-Amino-5-chlorobenzaldehyde

HRID 1636659Notes

Reaction equation

HRID 1636659 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[CH2:4][OH:5]>C(Cl)(Cl)Cl.[O-2].[Mn+4].[O-2]>[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

4

Reactant 1

HCID 5867542-Amino-5-chlorobenzyl alcohol

Product 1

HCID 27738982-Amino-5-chlorobenzaldehydeYield 88.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

2-Amino-5-chlorobenzyl alcohol (4.8 g, 30 mmol) and activated manganese (IV) oxide (21 g, 240 mmol) were refluxed in chloroform (100 mL) for 1 hour. The contents were allowed to cool, filtered through diatomaceous earth and concentrated in vacuo to afford the 2-amino-5-chlorobenzaldehyde as a dark solid (4.14 g, 81%): mp 74-76° C. 1H NMR (CDCl3, 300 MHz) 9.80 (s, 1H), 7.42 (s, 1H), 7.23 (d, 1H, J=7.0 Hz), 6.60 (d, 1H, J=7.0 Hz).

Workup

  1. temperatureto cool
  2. filtrationfiltered through diatomaceous earth
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-70470f4ea3ed418eb7dfba34f8e88bc1
Source dataset
uspto-grants-2000_03
Patent number
US06034256

Reaction notes

Loading…