Sodium Iodide → 5-Allyloxy-2-nitrobenzaldehyde

HRID 641845Notes

Reaction equation

HRID 641845 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].[I-].[Na+].C(N(C(C)C)[CH:18]([CH3:20])[CH3:19])C.C(Br)C=C>CC(C)=O>[CH2:20]([O:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8])[CH:18]=[CH2:19]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7841Allyl bromideHCID 392115-Hydroxy-2-nitrobenzaldehydeHCID 81531Diisopropylethylamine

Product 1

HCID 592590815-Allyloxy-2-nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 25 g (150 mmol) 5-hydroxy-2-nitro-benzaldehyde and 44.8 g (299 mmol) sodium iodide in 400 ml acetone are added 51.2 ml (299 mmol) N-ethyldiisopropylamine and 25.3 ml (299 mmol) allyl bromide. After stirring for 18 h at r.t. the reaction mixture is filtered and the solvent is evaporated. Extraction of the residue with 1 M aqueous hydrochloric acid/dichloromethane followed by chromatography (hexane/ethyl acetate) yields 5-allyloxy-2-nitro-benzaldehyde.

Workup

  1. filtrationis filtered
  2. customthe solvent is evaporated
  3. extractionExtraction of the residue with 1 M aqueous hydrochloric acid/dichloromethane

Sources & evidence

ORD record
ord-aa38b306df134272b5a2355778f6283e
Source dataset
uspto-grants-2010_04
Patent number
US07696216B2

Reaction notes

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