Methyl iodide → HCID 11148462, compound

HRID 859865Notes

Reaction equation

HRID 859865 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[CH2:7](I)[CH2:8][CH2:9][CH3:10].O[C:13]1[CH:20]=[C:19]([OH:21])[CH:18]=[CH:17][C:14]=1[CH:15]=[O:16].CI>CN(C)C=O>[CH2:7]([O:21][C:19]1[CH:20]=[CH:13][C:14]([CH:15]=[O:16])=[C:17]([O:4][CH3:1])[CH:18]=1)[CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 72132,4-DihydroxybenzaldehydeHCID 10962Butyl iodideHCID 11430Potassium Carbonate

Product 1

HCID 11148462HCID 11148462, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (1.50 g, 10.9 mmol) and butyl iodide (666 mg, 3.6 mmol) were added to a solution of 2,4-dihydroxybenzaldehyde (500 mg, 3.6 mmol) in dimethylformamide (5 ml), and they were stirred at room temperature for 2 hours. Then methyl iodide (2.57 ml) was added to the reaction mixture, and they were stirred at room temperature for 12 hours. After the extraction with ethyl acetate followed by the silica gel chromatography, 4-butoxy-2-methoxybenzaldehyde (yield: 233 mg, 31%) was obtained in the form of a colorless oil.

Workup

  1. stirringwere stirred at room temperature for 12 hours
  2. extractionAfter the extraction with ethyl acetate

Sources & evidence

ORD record
ord-16431baa445e4a28ba8b592d3f0aaa94
Source dataset
uspto-grants-2006_12
Patent number
US07153850B2

Reaction notes

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