Methyl iodide → 3-Hydroxy-5-methoxybenzaldehyde

HRID 2389693Notes

Reaction equation

HRID 2389693 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:10])[CH:9]=1)[CH:5]=[O:6].[H-].[Na+].I[CH3:14]>CN(C=O)C.Cl>[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][CH3:14])[CH:9]=1)[CH:5]=[O:6]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 943653,5-Dihydroxybenzaldehyde

Product 1

HCID 53145613-Hydroxy-5-methoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 3,5-dihydroxybenzaldehyde (1.0 g, 7.24 mmol) in DMF (20 mL) is treated with sodium hydride (319 mg, 8.0 mmol, 60% dispersion in mineral oil) at 0° C. After warming to RT and stirring 0.5 h, the reaction is treated with iodomethane (0.50 mL, 8.0 mmol) via syringe and stirred 16 h. It is then diluted with 1 M HCl (100 mL) and extracted into EtOAc (50 mL). The EtOAc phase is washed with 1 M HCl (50 mL), water (2×50 mL) and brine (50 mL), dried over Na2SO4 then the EtOAc removed in vacuo. The title compound is obtained after chromatography (gradient elution—0-50% EtOAc in heptane).

Workup

  1. stirringstirred 16 h
  2. extractionextracted into EtOAc (50 mL)
  3. washThe EtOAc phase is washed with 1 M HCl (50 mL), water (2×50 mL) and brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. customthe EtOAc removed in vacuo

Sources & evidence

ORD record
ord-dda47ee688f44c77bc6bf3ed673e6420
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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