Sulfuric Acid → Methyl 6-hydroxy-2,5,7,8-tetramethylchroman-2-acetate

Participants

Reaction Steps

To a suspension of 10.0 g (37.83 mM) of 6-hydroxy-2,5,7,8-tetramethylchroman-2-acetic acid in methanol (50 ml) was added 0.5 ml (6 mM) of concentrated sulfuric acid at room temperature and the mixture was stirred for 3 days. To this reaction mixture was added a saturated aqueous solution of sodium hydrogen carbonate at 0° C. until the pH had been brought to 5-7 and the solvent was then distilled off under reduced pressure. The residue was diluted with water and extracted with diethyl ether. The organic layer was washed with saturated aqueous solution of sodium chloride and dried over MgSO4. The solvent was then distilled off under reduced pressure to provide the title compound as tan-colored oil.

Provenance & Evidence