Nitric Acid → HCID 21459100, compound

HRID 2260212Notes

Reaction equation

HRID 2260212 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:12])[CH:9]([CH3:11])[CH3:10])=[CH:4][C:3]=1[O:13][CH3:14].[N+:15]([O-])([OH:17])=[O:16]>C(O)(=O)C.C(Cl)Cl>[OH:1][C:2]1[C:7]([N+:15]([O-:17])=[O:16])=[CH:6][C:5]([C:8](=[O:12])[CH:9]([CH3:10])[CH3:11])=[CH:4][C:3]=1[O:13][CH3:14]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 235144541-(4-Hydroxy-3-methoxyphenyl)-2-methyl-1-propanone

Product 1

HCID 21459100HCID 21459100, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 6344DichloromethaneSolvent

Procedure

15.0 g of 4'-hydroxy-3'-methoxy-2-methylpropiophenone are dissolved in 300 ml of glacial acetic acid and 7.65 ml of 50.5 percent nitric acid (11.2N) in 40 ml of glacial-acetic acid are added dropwise thereto while stirring within 15 minutes. After 15 minutes the reaction mixture is poured into ice-water and the separated crystals are filtered under suction, washed with water and dissolved in methylene chloride. The solution is dried over sodium sulfate and evaporated. The crude product obtained is taken up in methylene chloride and filtered over 100 g of silica gel. The thus-obtained crystals are recrystallized from methylene chloride/n-hexane. There is obtained 4'-hydroxy-3'-methoxy-2-methyl-5'-nitropropiophenone in the form of yellow crystals of m.p. 85°-87°.

Workup

  1. filtrationthe separated crystals are filtered under suction
  2. washwashed with water
  3. dissolutiondissolved in methylene chloride
  4. dry with materialThe solution is dried over sodium sulfate
  5. customevaporated
  6. customThe crude product obtained
  7. filtrationfiltered over 100 g of silica gel
  8. customThe thus-obtained crystals are recrystallized from methylene chloride/n-hexane

Sources & evidence

ORD record
ord-2e3866882fec4c1f9fb7c5693b8de5dc
Source dataset
uspto-grants-1995_12
Patent number
US05476875

Reaction notes

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