Acetic Acid → 2,3-dihydrobenzofuran-4-ol

Participants

Reaction Conditions

Reaction Steps

The product of Step 2 (39.25 g) was dissolved in THF (0.5 L) and cooled to −78° C. nBuLi (2.5M in hexanes, 300 mL) was then added dropwise over 30 minutes and the reaction stirred at −70° C. for an additional 45 minutes. The solution was then warmed to 0° C. over 10 minutes and stirred at this temperature for 1 hour. Glacial acetic acid (16 mL) was added followed by 1N NaOH (160 mL) and the layers allowed to separate. The organics were extracted with 1N NaOH (2×80 mL) and the combined aqueous fractions were then washed with TBME (160 mL). TBME (240 mL) was then added and the aqueous layer acidified with 6N HCl. The aqueous layer was re-extracted with TBME (240 mL), and the combined organics stirred over activated charcoal (5 g) for 15 minutes, filtered through Celite, and concentrated in vacuo. The crude product was crystallized from toluene and heptane to yield the title compound (16.8 g, 99%).

Provenance & Evidence