Lithium hydroxide, monohydrate → 2-(2-Ethynylphenyl)acetic acid

Participants

Reaction Steps

To a solution of ester 319 (4.65 g, 18.9 mmol) in 1:1 THF/methanol (100 mL) was added lithium hydroxide monohydrate (1.60 g, 38.1 mmol) in water (25 mL) and the mixture was stirred at r.t. for 30 min. It was then partially concentrated, the aqueous residue was washed with ether, then acidified with 3M HCl (aq) and extracted with ethyl acetate. The organic extract was washed with water, dried (anhydrous MgSO4), filtered and concentrated. The residue was dissolved in ethyl acetate, run through a short plug of silica gel, and concentrated to provide 320 (2.77 g, 92% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 12.40 (br s, 1H); 7.45 (d, J=8.0 Hz, 1H), 7.37-7.24 (m, 3H), 4.36 (s, 1H); 3.72 (s, 2H). LCMS: (M+Na) 183.1

Provenance & Evidence