Nitric Acid → 1-(2-Hydroxy-5-nitrophenyl)-2-methylpropan-1-one

HRID 1528165Notes

Reaction equation

[N+:1]([O-:4])([OH:3])=[O:2].[OH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[O:16])[CH:13]([CH3:15])[CH3:14].CCCCCCC.C(OCC)(=O)C>C(O)(=O)C>[OH:5][C:6]1[CH:11]=[CH:10][C:9]([N+:1]([O-:4])=[O:2])=[CH:8][C:7]=1[C:12](=[O:16])[CH:13]([CH3:14])[CH3:15].[OH:5][C:6]1[C:11]([N+:1]([O-:3])=[O:2])=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[O:16])[CH:13]([CH3:14])[CH3:15]

Participants

Conditions

Temperature: 5 °C

Procedure

1.6 ml of fuming nitric acid were added, over the course of 20 minutes, to a solution of 4.1 g of 1-(2-hydroxyphenyl)-2-methylpropan-1-one in 25 ml of acetic acid cooled to 5° C. The reaction medium was stirred at ambient temperature for 5 hours (followed by TLC, 10/1 heptane/ethyl acetate). The reaction was stopped before all the 1-(2-hydroxyphenyl)-2-methylpropan-1-one was consumed. The reaction medium was diluted with 70 ml of water and then extracted with ethyl acetate (4:1, 3×50 ml). The organic phases were combined, washed with water (20 ml) and then with a saturated sodium chloride solution (25 ml), and dried over magnesium sulfate. The solvent was evaporated off and the residue was chromatographed on silica. 1.40 g of 1-(2-hydroxy-5-nitrophenyl)-2-methylpropan-1-one and 1.2 g of 1-(2-hydroxy-3-nitrophenyl)-2-methylpropan-1-one were obtained.

Workup

customwas consumed
additionThe reaction medium was diluted with 70 ml of water
extractionextracted with ethyl acetate (4:1, 3×50 ml)
washwashed with water (20 ml)
dry with materialwith a saturated sodium chloride solution (25 ml), and dried over magnesium sulfate
customThe solvent was evaporated off
customthe residue was chromatographed on silica

Sources & evidence

ORD record: ord-ac778bd2713a42988a1ceb72af474de8
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090596B2

Reaction notes

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