Lithium Hydroxide → 3-((Di-tert-butoxyphosphoryloxy)methyl)benzoic acid

Participants

Reaction Steps

To a solution of methyl 3-((di-tert-butoxyphosphoryloxy)methyl)benzoate (0.1 g, 0.3 mmol) in THF (3 mL), methanol (3 mL), water (3 mL) was added lithium hydroxide (0.035 g, 0.81 mmol). The reaction mixture was stirred at rt for 1 h. After this time, the organic solvents were removed under reduced pressure, and EtOAc (30 mL) was added to the residual material followed by acetic acid (30%). The organic layer was washed with water (2×10 mL), dried over Na2SO4 and concentrated under vacuum to afford 3-((di-tert-butoxyphosphoryloxy)methyl)benzoic acid (80 mg, 0.23 mmol). 1H NMR (400 MHz, DMSO-d6): 1.41 (s, 18H), 5.00 (d, J=8, 2H), 7.52 (t, J=7.6, 1H), 7.62 (d, J=7.6, 1H), 7.90 (d, J=8.0, 1H), 7.99 (s, 1H). LCMS-m/z: 343.2.

Provenance & Evidence