Methanol → 3-(Benzyloxy)-4-nitrobenzenecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

Cmpd 2 (1.53 g, 1.0 eq) was dissolved in THF (52.8 mL) and MeOH (26.4 mL) in a round bottom flask, followed by addition of 2N NaOH (13.2 mL, 5.0 eq). The reaction was heated at 60° C. for 3 hours, occasionally opening the flask to release pressure. The reaction was monitored by TLC (5% MeOH:95% DCM). The resulting mixture was concentrated, and the residue was dissolved in water and acidified to pH=2-3 with 1N HCl. The acidic solution was extracted with AcOEt 3×, dried over Na2SO4, filtered and concentrated to afford Cmpd 3 as a light yellowish solid (1.25 g, 96% yield). Analytic: 1H NMR (DMSO d6, 500 mHz): δ 7.99 (d, 1H), 7.87 (s, 1H), 7.66 (dd, 1H), 7.46-7.40 (m, 4H), 7.33 (m, 1H), 5.39 (s, 2H). LCMS (C18, 2-98% CH3CN in 0.1% TFA/H2O over 6 min); Calculated mass for C14H11NO5 (M+H)+274.06. found by LC-MS 274.

Provenance & Evidence