Lithium hydroxide, monohydrate → 2-(3-(Diethoxyphosphoryl)phenyl)acetic acid

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Reaction Steps

A mixture of ethyl 2-(3-(diethoxyphosphoryl)phenyl)acetate, 35i-c, (26 g, 86.7 mmol) and LiOH.H2O (5.5 g, 130 mmol) in ethanol (40 mL) and H2O (40 mL) was stirred overnight. The resulting mixture was concentrated and washed by ethyl acetate. The aqueous layers were adjusted to about pH 1-2 with HCl. The mixture was extracted by ethyl acetate. The combined organic layers were washed by brine, dried over Na2SO4 and concentrated to afford the title compound, 35i-d, as brown oil (19 g, 81%). 1H NMR (300 MHz, CDCl3) δ1.15-1.25 (m, 6H), 3.68 (s, 2H), 3.95-4.06 (m, 4H), 7.43-7.64 (m, 4H), 12.32 (s, 1H). LC-MS (M+H)+ 273.

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