Methylhydroquinone → 4-Hydroxy-3-methylphenyl acetate

HRID 131752

Reaction equation

HRID 131752 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[OH:8][C:9]1[CH:14]=[CH:13]C(O)=[C:11](C)[CH:10]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[C:5]([O:4][C:1]1[CH:11]=[CH:10][C:9]([OH:8])=[C:14]([CH3:13])[CH:2]=1)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 7253MethylhydroquinoneHCID 7918Acetic AnhydrideHCID 10796Cesium carbonate

Product 1

HCID 155324474-Hydroxy-3-methylphenyl acetateYield 3.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Acetic anhydride (4.73 gm, 4.37 mL, 46.3 mMol) was added dropwise to a mixture of 4-hydroxy-2-methylphenol (5 gm, 46.3 mMol) and cesium carbonate (15.1 gm, 46.3 mMol) in acetonitrile (50 mL). After stirring overnight, the mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 5:1 pentane:ethyl acetate. Fractions containing product were combined and concentrated under reduced pressure to provide 0.24 gm (3%) of the desired compound.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washeluting with 5:1 pentane
  4. additionFractions containing product
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9791b4f6a2c1460ebe7e3ef50b834101
Source dataset
uspto-grants-2008_06
Patent number
US07384983B2

Linked notes

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