Formaldehyde → 2-Hydroxy-3,4,6-trimethylbenzaldehyde

HRID 854952Notes

Reaction equation

HRID 854952 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1[OH:10].[CH2:11]=[O:12].[Mg+2].[Cl-].[Cl-]>C(#N)C>[OH:10][C:3]1[C:4]([CH:11]=[O:12])=[C:5]([CH3:9])[CH:6]=[C:7]([CH3:8])[C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 127692,3,5-TrimethylphenolHCID 5360315Magnesium Chloride

Product 1

HCID 113211462-Hydroxy-3,4,6-trimethylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2,3,5-trimethylphenol (11.2 g, 82.0 mmoles) in 400 mL of acetonitrile was added paraformaldehyde (17.2 g, 574 mmoles), anhydrous MgCl2 (11.7 g, 123 mmoles), and TEA (43 mL 31 g, 308 mmoles). The mixture was refluxed for 6 h with stirring. After cooling, the mixture was partially concentrated, water added, and the mixture acidified with dilute aqueous HCl. The mixture was extracted with three times with Et2O, the combined organic extracts washed with brine, dried over Na2SO4, filtered, and concentrated. Chromatography of the residue over silica gel using DCM as eluent gave 6-hydroxy-2,4,5-trimethylbenzaldehyde, 8.8 g, as an oil.

Workup

  1. temperatureThe mixture was refluxed for 6 h
  2. temperatureAfter cooling
  3. concentrationthe mixture was partially concentrated
  4. additionwater added
  5. extractionThe mixture was extracted with three times with Et2O
  6. washthe combined organic extracts washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9108c67313a9448182da326457150ba3
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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