4-Hydroxy-3-nitroacetophenone

Yellow Solid

Phenol (94 mg, 1 mmol) dissolved in 3 mL glacial acetic acidin a 50 mL test tube was treated with solid Y(NO3)3.6H2O(383 mg, 1 mmol) with constant shaking at RT for 10 min.The reaction was monitored by TLC at 10percent EtOAc inPetroleum benzene. Ice-cold water (30 mL) was added to thereaction mixture after completion of reaction and left for 15min. Solid was collected by filtration and washed with water.Solid product isolated in this way was used for analysis withoutfurther purification. Experimental procedure for the synthesisof compounds 2a–2e is mentioned in the SupportingInformation.STR84 EXAMPLE 5 General procedure: To a solution of 4-hydroxybenzophenone or 4-hydroxyacetophenone (1.26 mmol) in dichloromethane(15 mL), potassium hydrogen sulfate (6.82 mmol), sodiumnitrate (7.32 mmol), and 0.875 g of wet silica 50percent p/p wasadded. The slurry was was left under constant stirring atroom temperature until the completion of the reaction, checked by TLC (hexane/ethyl acetate, 8:2v/v). Then themixture was filtered through silica, the solid was washedwith dichloromethane and the solvent removed underreduced pressure. The products were then purified byrecrystallization.Phenol (94 mg, 1 mmol) dissolved in 3 mL glacial acetic acidin a 50 mL test tube was treated with solid Y(NO3)3.6H2O(383 mg, 1 mmol) with constant shaking at RT for 10 min.The reaction was monitored by TLC at 10% EtOAc inPetroleum benzene. Ice-cold water (30 mL) was added to thereaction mixture after completion of reaction and left for 15min. Solid was collected by filtration and washed with water.Solid product isolated in this way was used for analysis withoutfurther purification. Experimental procedure for the synthesisof compounds 2a-2e is mentioned in the SupportingInformation.STR84 5.00 g (36.7 m mole) of 4-acetylphenol was dissolved in 50 ml of sulfuric acid. To the mixture solution 3.10 ml (40.7 m mole) of nitric acid (60%, d=1.38) was gradually added dropwise, keeping the reaction temperature at 2-10 C. and cooling with ice under stirring. Then the mixture solution was stirred at the same temperature. After the reaction, the reaction mixture was poured into ice water to precipitate a crystal. The crystal was filtered, washed with water and recrystallized from methanol to obtain 5.84 g of 2-nitro-4-acetylphenol (Yield: 79.8%).EXAMPLE 5 2-(4-decyloxyphenyl)-5-octyloxybenzoxazole (Example Compound No. 1-114) was synthesised through the following reaction schemes. STR81 5.00 g (36.7 ml) of 4-acetylphenol was dissolved in 50 ml of sulfuric acid. To the solution, 3.10 ml (40.7 mM) of nitric acid (60%, density=1.38) was gradually added dropwise under stirring at 2-10 C. on an ice bath, followed by stirring at 2-10 C. after the addition. After the reaction, the reaction mixture was poured into ice water to precipitate a crystal. The crystal was recovered by filtration and washed with water, followed by recrystallization from methanol to obtain 5.84 g of 2-nitro-4-acetylphenol (Yield: 79.8%).General procedure: To a solution of 4-hydroxybenzophenone or 4-hydroxyacetophenone (1.26 mmol) in dichloromethane(15 mL), potassium hydrogen sulfate (6.82 mmol), sodiumnitrate (7.32 mmol), and 0.875 g of wet silica 50% p/p wasadded. The slurry was was left under constant stirring atroom temperature until the completion of the reaction, checked by TLC (hexane/ethyl acetate, 8:2v/v). Then themixture was filtered through silica, the solid was washedwith dichloromethane and the solvent removed underreduced pressure. The products were then purified byrecrystallization.In particular, compounds of formula I may be selected from the list comprising4-methoxy-2-nitrophenol, , wherein the compound is selected from4-methoxy-2-nitrophenol,

Molecular Weight:181.15
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:181.03750770
Monoisotopic Mass:181.03750770
Topological Polar Surface Area:83.1
Heavy Atom Count:13
Complexity:223
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes