2-Hydroxy-4-Methoxybenzaldehyde → 5-Methoxy-2-methylphenol

HRID 1296076Notes

Reaction equation

HRID 1296076 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.C([O-])=O.[NH4+]>[Pd].C(O)(=O)C>[CH3:11][O:10][C:8]1[CH:7]=[CH:6][C:3]([CH3:4])=[C:2]([OH:1])[CH:9]=1

Participants

5

Reactant 2

HCID 696002-Hydroxy-4-MethoxybenzaldehydeHCID 2723923Ammonium formate

Product 1

HCID 109535825-Methoxy-2-methylphenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

2-Hydroxy-4-methoxy-benzaldehyde (3 g, 19.7 mmol), ammonium formate (6.2 g, 99 mmol) and palladium/carbon (900 mg @ 10%) were added to 26 ml glacial acetic acid and heated at 110° C. for 1 h. The reaction was cooled, filtered, and diluted with water (100 ml). The crude product was extracted with chloroform (3×50 ml), washed with water, brine, and dried over anhydrous sodium sulfate. The resulting solution was concentrated and used for the next step without further purification. MS m/z 139 (M+1).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. additiondiluted with water (100 ml)
  4. extractionThe crude product was extracted with chloroform (3×50 ml)
  5. washwashed with water, brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationThe resulting solution was concentrated
  8. customused for the next step without further purification

Sources & evidence

ORD record
ord-ecee7672379342faafef2754ed37c86b
Source dataset
uspto-grants-2007_07
Patent number
US07244763B2

Reaction notes

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