Pyridine → 3-hydroxy-4-(2-methoxyethoxy)benzaldehyde O-methyloxime

HRID 2236570Notes

Reaction equation

HRID 2236570 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][O:13][CH3:14])[CH:5]=O.CC[O:17][CH2:18]C.[N:20]1C=CC=CC=1>CCO>[CH3:18][O:17][N:20]=[CH:5][C:4]1[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH2:12][O:13][CH3:14])=[C:2]([OH:1])[CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 3283Diethyl EtherHCID 426255193-Hydroxy-4-(2-methoxyethoxy)benzaldehyde

Product 1

HCID 722508733-hydroxy-4-(2-methoxyethoxy)benzaldehyde O-methyloximeYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An amount of 3-hydroxy-4-(2-methoxyethoxy)benzaldehyde (1.24 g, 6.32 mmol) in 20 mL of EtOH and 10 mL of pyridine is added methoxy]amine hydrochloride (1.06 g, 12.64 mmol). The reaction mixture is stirred at room temperature over weekend. Solvent is removed under vacuum to give colorless oil which is added ether, washed twice with saturated NaHCO3 solution, once with brine, dried over Mg2SO4, filtered and evaporated to give colorless oil. Leaving this oil overnight at room temperature gave 1.15 g (81.0% yield) of colorless solid: mp: 63-64° C.; MS (ESI) m/z 226.1 (M+H)+1

Workup

  1. customSolvent is removed under vacuum
  2. customto give colorless oil which
  3. washwashed twice with saturated NaHCO3 solution, once with brine
  4. dry with materialdried over Mg2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give colorless oil
  8. customLeaving this oil overnight at room temperature

Sources & evidence

ORD record
ord-bed74967eaa54242b39def900d23ad2f
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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