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

HRID 524071

Reaction equation

HRID 524071 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]+.

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-bb2fe668888f4e2689fdc4ae23fd131e
Source dataset
uspto-grants-2016_05
Patent number
US09340514B2

Linked notes

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