3-(Benzyloxy)-4-nitrobenzenecarboxylic acid synthesis

5synthesis methods

Product Name:3-(Benzyloxy)-4-nitrobenzenecarboxylic acid
CAS Number:14617-29-9
Molecular formula:C14H11NO5
Molecular Weight:273.24

209528-69-8
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3-(Benzyloxy)-4-nitrobenzenecarboxylic acid

14617-29-9
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Yield:14617-29-9 96%

Reaction Conditions:

with sodium hydroxide in tetrahydrofuran;methanol at 60; for 3 h;

Steps:

1b 3-(benzyloxy)-4-nitrobenzoic acid (3)

Example 1b
3-(benzyloxy)-4-nitrobenzoic acid (3)
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.