2-(3-HYDROXY-4-NITROPHENYL)ACETIC ACID synthesis
- Product Name:2-(3-HYDROXY-4-NITROPHENYL)ACETIC ACID
- CAS Number:152148-79-3
- Molecular formula:C8H7NO5
- Molecular Weight:197.14
621-37-4
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Yield:-
Reaction Conditions:
with nitric acid in water at 20; for 0.5 h;
Steps:
General procedure: An appropriate phenol compound 8a-13a (1 mmol) was mixed with 60% HNO3 (4.8 mmol). Theresulting suspension was stirred at room temperature for 10 min for 8a and 9a, for 30 min for 10a, 12aand 13a, or overnight for 11a, leading eventually to an intensively dark red solution. HPLC analysisconfirmed the absence of starting material and the presence of 3 major products corresponding mostlikely to nitro derivatives resulting from nitration at the o- and p-positions of the hydroxy group fromthe m-substituted phenols 8a, 10a and 12a, but only one product from the p-substituted phenols 9a,11a and 13a. The crude nitrophenol 8b or 9b was diluted with water (20 mL) and applied onto aDowex 50W-X2 (200-400 mesh) column (1.5 cm × 6 cm, H+ form, equilibrated with water).The column was washed with water (100 mL) and then the product was eluted with 2 M HCl(20 mL/fraction). Fractions containing the target compound were combined and evaporated to drynessto give a yellow powder. After the nitration of phenols 10a, 12a and 13a, the reaction mixture (10b,12b and 13b) was diluted with H2O (20 mL) and extracted with ethyl acetate (2 × 100 mL). Thecombined organic extract was washed with water (2 × 50 mL), dried with Na2SO4 and evaporatedunder reduced pressure. The nitration of 11a afforded 11b as an orange powder in the reaction mixture.After the filtration, the powder was washed with water and dried under reduced pressure to give a darkred powder 11b.
References:
Wakamatsu, Kazumasa;Tanaka, Hitomi;Tabuchi, Keisuke;Ojika, Makoto;Zucca, Fabio A.;Zecca, Luigi;Ito, Shosuke [Molecules,2014,vol. 19,# 6,p. 8039 - 8050]
61161-83-9
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