5-isopropyl-2-nitrophenol synthesis

Yield:153506-06-0 27%

Reaction Conditions:

with sodium nitrate;sulfuric acid;sodium nitrite in dichloromethane;

Steps:

125.a a)

a) Preparation of 2-nitro-5-isopropylphenol 3-isopropylphenol (3.00 g, 22 mmol) was dissolved in methylene chloride(40 ml) followed by the addition of sodium nitrate (2.06 g, 24 mmol). The addition of sulfuric acid (25 mL/3M) is then made, followed by addition of a catalytic amount of sodium nitrite. The mixture was allowed to stir. After 24 h, the reaction mixture is diluted with methylene chloride and extracted with water. The organic layer is dried over MgSO₄ and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4% MeOH/CH₂ Cl₂) gave the desired product(1.09 g, 27%). ¹ H NMR (CD3COCD₃): δ 7.95 (d, 1H), 7.62 (d, 1H), 7.11 (d, 1H), 2.95 (m, 1H), 1.24 (d, 6H).

References:

US5886044,1999,A