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

HRID 56481

Reaction equation

HRID 56481 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 room temperature overnight. 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-003cfd564bcb451a939941a0e045f637
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Linked notes

Loading…