Acetic Acid → 5-Methoxy-2-methylphenol

HRID 1822341Notes

Reaction equation

HRID 1822341 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)C.[H][H]>C(O)C.[Pd]>[CH3:11][O:10][C:8]1[CH:7]=[CH:6][C:3]([CH3:4])=[C:2]([OH:1])[CH:9]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 696002-Hydroxy-4-MethoxybenzaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 109535825-Methoxy-2-methylphenolYield 87.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-hydroxy-4-methoxy-benzaldehyde (5.00 g, 32.86 mmol) and palladium under carbon (10%) (3.50 g, 3.28 mmol) in ethanol (32 mL) and acetic acid (3 mL) is stirred under 60 psi of hydrogen. After stirring overnight, the mixture is filtered off through Celite and washed with methanol. The mixture is concentrated under reduced pressure, and purified by flash chromatography by eluting with hexane:ethyl acetate 2:1 to afford the title compound (3.96 g, 87%). Rf=0.58 (hexane:ethyl acetate 2:1). δ1HNMR (300 MHz, CDCl3): 2.18 (s, 3H), 3.75 (s, 3H), 6.42 (m, 2H), 7.00(d, 1H, J=8.9 Hz).

Workup

  1. filtrationthe mixture is filtered off through Celite
  2. washwashed with methanol
  3. concentrationThe mixture is concentrated under reduced pressure
  4. custompurified by flash chromatography
  5. washby eluting with hexane:ethyl acetate 2:1

Sources & evidence

ORD record
ord-f2fb2a850b8f4b9db58b97254185445f
Source dataset
uspto-grants-2009_10
Patent number
US07608639B2

Reaction notes

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