2-(3-Methyl-5-nitrophenyl)acetic acid synthesis

Yield:-

Reaction Conditions:

with sulfuric acid;water

Steps:

5.3. (3-Methyl-5-nitrophenyl)acetic acid (9a)

To a stirred suspension of 8 (3.4 mmol) in water (2.5 mL) was added concd H₂SO₄ (2.5 mL). After stirring for 1.5 h under reflux, the reaction mixture was cooled to room temperature, poured into water and extracted with EtOAc (×2). The combined organic layers were washed with water, brine, dried over Na₂SO₄ and concentrated in vacuo to yield 9a (130 mg, 20% in 2 steps) as a pale orange solid, which was used for the next reaction without further purification; TLC R_f = 0.50 (CHCl₃/CH₃OH, 9:1); ¹H NMR (300 MHz, CDCl₃) δ 7.98 (s, 2H), 7.44 (s, 1H), 3.74 (s, 2H), 2.47 (s, 3H).

References:

Iwahashi, Maki;Takahashi, Eiji;Tanaka, Motoyuki;Matsunaga, Yoko;Okada, Yutaka;Matsumoto, Ryoji;Nambu, Fumio;Nakai, Hisao;Toda, Masaaki [Bioorganic and Medicinal Chemistry,2011,vol. 19,# 18,p. 5361 - 5371] Location in patent:experimental part