HCID 10355440, compound → HCID 10131175, compound

Participants

Reaction Steps

Refluxing 22.36 g of the above material (see Step C) in 100 ml of methanol and 100 ml of 2N sodium hydroxide for 24 hours is followed by acidification with 120 ml of 2N hydrochloric acid, evaporation of methanol, and extraction with ethyl acetate (twice). The extract is washed with water and acidic product is extracted into a sodium bicarbonate solution, which upon acidification is reextracted with ethyl acetate. The extract is dried over sodium sulfate, filtered and evaporated. The resulting solid is recrystallized from ethyl acetate/heptane to give 16.40 g (77%) of 2,3-dihydro-5-hydroxy-2,2,4,6,7-pentamethyl-1-benzofuran-3-carboxylic acid, m.p. 161°-164° C. Elemental analysis, IR, UV, and 1H-NMR spectra confirm the structure.

Provenance & Evidence