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

HRID 2274215Notes

Reaction equation

HRID 2274215 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-3c4619a69ebf425f9c1b1b4a1936e555
Source dataset
uspto-grants-2015_09
Patent number
US09126951B2

Reaction notes

Loading…