(2-Amino-4-methoxyphenyl)methanol → 2-Amino-4-methoxybenzaldehyde

HRID 2404054Notes

Reaction equation

HRID 2404054 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH2:10][OH:11]>ClCCl.[O-2].[Mn+2]>[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]=[O:11]

Participants

4

Reactant 1

HCID 45090899(2-Amino-4-methoxyphenyl)methanol

Product 1

HCID 3235032-Amino-4-methoxybenzaldehydeYield 35.3%

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (2-amino-4-methoxyphenyl)methanol (20 g, 131.0 mmol) and manganese oxide (68 g, 786.0 mmol) in dichloromethane (300 mL) was stirred at RT overnight. LCMS showed the reaction was completed. The solid was filtered off, and the filtrate was concentrated. The residue was purified by silica gel chromatography (petroleum ether:ethyl acetate=6:1) to give the title compound (7 g, 35%) as a yellow solid. MS (ES+) C8H9NO2 requires: 151. found: 152 [M+H]+. Synthesis of 2-amino-5-bromo-4-methoxybenzaldehyde

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel chromatography (petroleum ether:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-4cc2fdf3d77c406a822075e3031bbdc0
Source dataset
uspto-grants-2014_08
Patent number
US08802697B2

Reaction notes

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