Methanol → 3,5-Dimethyl-4-hydroxybenzaldehyde

HRID 2260033Notes

Reaction equation

HRID 2260033 reaction equation
[C:1]1([CH3:10])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[OH:9].CC1C=CC2C=CC3C=CC(C)=NC=3C=2N=1.[OH2:27].CO>C(OCC)(=O)C.Cl[Cu]>[CH3:10][C:1]1[CH:6]=[C:5]([CH:4]=[C:3]([CH3:8])[C:2]=1[OH:9])[CH:7]=[O:27]

Participants

6

Reactant 3

HCID 887MethanolHCID 106982,4,6-TrimethylphenolHCID 162112342,9-Dimethyl-1,10-phenanthroline hydrate

Product 1

HCID 752223,5-Dimethyl-4-hydroxybenzaldehydeYield 6,278.4%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 13.622 g(100 mmol) of mesitol, 285 mg (1.26 mmol) of neocuproine hydrate, 503 mg (5.0 mmol) of CuCl and 120 mL of methanol was stirred at ambient temperature for 9 hours under an oxygen blanket. The reaction mixture was then diluted with ethyl acetate and filtered. The methanol was stripped off and the residue diluted with additional ethyl acetate. The solution was washed twice with a 1% solution of ethylenediaminetetraacetic acid trisodium salt (EDTA-Na3.2H2O), water and brine, dried over MgSO4 and concentrated. There was obtained 13.92 g of an orange-gold solid which was shown by 1H NMR and GC to contain 11.88 g (79.2% yield) of 3,5-dimethyl-4-hydroxybenzaldehyde (DMHB).

Workup

  1. filtrationfiltered
  2. additionthe residue diluted with additional ethyl acetate
  3. washThe solution was washed twice with a 1% solution of ethylenediaminetetraacetic acid trisodium salt (EDTA-Na3.2H2O), water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThere was obtained 13.92 g of an orange-gold solid which

Sources & evidence

ORD record
ord-1667c76ec710476d93238c4239622002
Source dataset
uspto-grants-1995_12
Patent number
US05475156

Reaction notes

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