Methylhydroquinone → 4-Hydroxy-3-methylphenyl acetate

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

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.