Methane → 2,4-Dimethylresorcinol

HRID 1744282Notes

Reaction equation

HRID 1744282 reaction equation
[OH:1][C:2]1[C:9]([CH3:10])=[C:8]([OH:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[H][H].C>CO.C(O)(=O)C.[Pd]>[OH:11][C:8]1[CH:7]=[CH:6][C:3]([CH3:4])=[C:2]([OH:1])[C:9]=1[CH3:10]

Participants

7

Reactant 3

HCID 297Methane2×HCID 803952,4-Dihydroxy-3-methylbenzaldehydeHCID 178418361HCID 178418361, compound2×

Product 1

HCID 694522,4-DimethylresorcinolYield 30.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

1 g (6.5 mmol) of 2,4-dihydroxy-3-methylbenzaldehyde is hydrogenated, at 3 bar hydrogen pressure for 24 h, with 100 mg of Pd on active charcoal (10%) in 100 ml of methanol and 1 ml of glacial acetic acid. A further 100 mg of Pd on active charcoal (20%) are added and the mixture is hydrogenated at 3 bar hydrogen pressure for 12 h. The catalyst is filtered off, the solvent is removed in vacuo and the residue is purified by chromatography (dichloromethane/acetone). 274 mg (30%) of 1,3-dihydroxy-2,4-dimethylbenzene are obtained.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe solvent is removed in vacuo
  3. customthe residue is purified by chromatography (dichloromethane/acetone)

Sources & evidence

ORD record
ord-fd45da4899104c9da4521450e27bfd02
Source dataset
uspto-grants-2006_03
Patent number
US07015246B2

Reaction notes

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