Ammonium nitrate → 5-Chloro-2-hydroxy-4-methoxybenzaldehyde

HRID 493201Notes

Reaction equation

HRID 493201 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Cl:12]N1C(=O)CCC1=O.[N+]([O-])([O-])=O.[NH4+]>C(#N)C>[Cl:12][C:7]1[C:8]([O:10][CH3:11])=[CH:9][C:2]([OH:1])=[C:3]([CH:6]=1)[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 22985Ammonium nitrateHCID 31398ChlorosuccinimideHCID 696002-Hydroxy-4-Methoxybenzaldehyde

Product 1

HCID 552533435-Chloro-2-hydroxy-4-methoxybenzaldehydeYield 21.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

2-Hydroxy-4-methoxy-benzaldehyde (0.974 g, 6.40 mmol) was dissolved in 10 mL of acetonitrile and treated with N-chlorosuccinimide (0.983 g, 1.15 eq.) and ammonium nitrate (0.102 g, 0.20 eq.), and the mixture was warmed to 70° C. for roughly 5 h. Evaporation of the solvent, followed by flash chromatography (SiO2, heptane/AcOEt=85/15), and direct crystallization from heptane/AcOEt, produced then 0.259 g of the title compound as white crystals.

Workup

  1. customEvaporation of the solvent
  2. customfollowed by flash chromatography (SiO2, heptane/AcOEt=85/15), and direct crystallization from heptane/AcOEt
  3. customproduced

Sources & evidence

ORD record
ord-19630f5060ce456b9439696f754f90a0
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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