Methyl iodide → 2-Hydroxy-4-Methoxybenzaldehyde

HRID 903107Notes

Reaction equation

HRID 903107 reaction equation
[CH:1](=[O:10])[C:2]1[C:3](=[CH:5][C:6](=[CH:8][CH:9]=1)[OH:7])[OH:4].[CH3:11]I>C[O-].[Na+]>[CH3:11][O:7][C:6]1[CH:5]=[C:3]([OH:4])[C:2](=[CH:9][CH:8]=1)[CH:1]=[O:10]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 72132,4-Dihydroxybenzaldehyde

Product 1

HCID 696002-Hydroxy-4-Methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Procedure

Beta-resorcyl aldehyde (13.8 grams) is dissolved in sodium methoxide (in amount equivalent to 2.3 grams of sodium), and 14.2 grams of methyl iodide are added. The mixture is refluxed for 4 hours. Alcohol (methanol) is distilled off and dilute HCl added. The resulting red liquid is separated from the aqueous layer, dried and steam distilled.

Workup

  1. temperatureThe mixture is refluxed for 4 hours
  2. distillationAlcohol (methanol) is distilled off
  3. additiondilute HCl added
  4. customThe resulting red liquid is separated from the aqueous layer
  5. customdried
  6. distillationsteam distilled

Sources & evidence

ORD record
ord-e7923aa21ceb47ccb1d9eb92d56cd4c9
Source dataset
uspto-grants-1980_10
Patent number
US04226792

Reaction notes

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