ethyl 3,4-dihydro-1H-2-benzopyran-1-acetate → 2-(3,4-dihydro-1H-2-benzopyran-1-yl)acetic acid

Participants

Reaction Steps

To a solution of (±)-isochroman-1-yl-acetic acid ethyl ester (1.90 g, 8.63 mmol, 1 eq.) in THF (40 mL) and MeOH (10 mL), 1M aq. NaOH soln. (17.3 mL, 17.3 mmol, 2 eq.) was added. The pale yellow solution was stirred at r.t. for 2 hours, then the organic solvents were removed in vacuo. The aq. layer was washed with AcOEt (1×10 mL). The aq. layer was acidified with 1N aq. HCl (pH=1). The resulting emulsion was extracted with DCM (3×25 mL). The comb. org. phases were dried over MgSO4 and concentrated in vacuo to give the title compound as a colorless oil that solidifies upon standing. The product was used without further purification.

Provenance & Evidence