Ethanol → Ethyl 2-(3-hydroxy-4-nitrophenyl)acetate
Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:11][C:12]([OH:14])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH2:15](O)[CH3:16]>Cl>[CH2:15]([O:13][C:12](=[O:14])[CH2:11][C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([OH:1])[CH:3]=1)[CH3:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of (3-hydroxy-4-nitro-phenyl)-acetic acid (4.0 g, prepared according to the procedure described by Meyer et al, J. Med. Chem., 1997, 40, pages 1049–1062) in ethanol (approximately 100 mL) was treated with concentrated hydrochloric acid (5–8 drops) was heated at reflux temperature for 3 hours then evaporated. The residue was dissolved in tert-butyl methyl ether and the solution was washed with saturated aqueous sodium bicarbonate solution, then with water, then dried, and then evaporated to give the title compound (5.0 g) as a light yellow solid.