Dimethyl Sulfate → HCID 54076170, compound

Participants

Reaction Steps

A mixture of phenol 5-hydroxy-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-one (7.16 g, 32.54 mmol), dimethylsulfate (6.16 g, 48.8 mmol) and potassium carbonate (13.5 g, 97.63 mmol) in acetone (160 mL) is refluxed under nitrogen for 3 days. After cooling, 3N sodium hydroxide (100 mL) is added and most of the acetone is evaporated under reduced pressure. The mixture is extracted with ethyl acetate (200 mL) and the organic layer is washed with 3N sodium hydroxide (2×100 mL), water, brine, dried (magnesium sulfate)and evaporated to dryness to give 7.52 g (99%) of 5-methoxy-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-one as a yellow solid which is used without purification for the next step. Rf=0.4 (heptane/ethyl acetate 90:10)

Provenance & Evidence