Methanol → HCID 2750802, compound

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Reaction Steps

Methyl 2-hydroxy-2-[2-nitrophenyl]acetate (FIG. 2; Compound 6) was prepared by dissolving crude acid 2-hydroxy-2-[2-nitrophenyl]acetic acid (entire amount) in methanol (100 ml). Sulfuric acid (5 drops) was added, and the mixture was refluxed for 2.5 hr. The solvent was then evaporated. The residue was taken up in ethyl acetate and extracted with saturated sodium bicarbonate, followed by water and brine. After drying over MgSO4, the solvent was evaporated to give 9.13 g (90%) of crude ester which was recrystallized from isopropyl ether to give 7.92 g (78%) of methyl 2-hydroxy-2-[2-nitrophenyl]acetate. mp. 69-71° C. 1H-NMR: 8.01 (d, J=8.19 Hz, 1H), 7.70-7.63 (m, 2H), 7.55-7.49 (m, 1H), 5.83 (d, J=4.88 Hz, 1H), 3.76 (s, 3H), 3.66 (d, J=4.89 Hz, 1H). HRMS(CI): calculated for C9H10NO5 [M+ +H] m/z=212.0559, observed 212.0555.

Provenance & Evidence