Acetic Acid → 1-(2-Hydroxy-3-nitrophenyl)-ethanone

HRID 1090782Notes

Reaction equation

HRID 1090782 reaction equation
O[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[N+:11]([O-])([OH:13])=[O:12].C(O)(=[O:17])C>>[CH3:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:6]=1[OH:17])=[O:4]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 68490alpha-Hydroxyacetophenone

Product 1

HCID 2700261-(2-Hydroxy-3-nitrophenyl)-ethanone

Procedure

10.0 g of 2-hydroxyacetophenone is dissolved in 60 ml of glacial acetic acid. 10.4 ml of nitric acid (specific gravity=1.40) is then added over 2 hours at room temperature. The mixture is stirred for 17 hours, then poured onto ice and the resulting precipitate (containing both the 3- and 5-nitro isomers) collected. The isomers are separated by HPLC to give 4.0 g of 2-hydroxy-3-nitroacetophenone.

Workup

  1. additionpoured onto ice
  2. customcollected
  3. customThe isomers are separated by HPLC

Sources & evidence

ORD record
ord-0767533cd67243319d1784af2d2c9586
Source dataset
uspto-grants-1992_01
Patent number
US05082849

Reaction notes

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