Nitric Acid → 2-Nitro-9,10-dihydrophenanthrene

HRID 68491Notes

Reaction equation

HRID 68491 reaction equation
[CH:1]1[C:14]2[CH2:13][CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[N+:15]([O-])([OH:17])=[O:16].O>C(O)(=O)C>[N+:15]([C:9]1[CH:8]=[CH:7][C:6]2[C:5]3[C:14](=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH2:13][CH2:12][C:11]=2[CH:10]=1)([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 130589,10-Dihydrophenanthrene

Product 1

HCID 792362-Nitro-9,10-dihydrophenanthreneYield 74%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

First, 300 g of 9,10-dihydrophenanthrene were dissolved in 2 L of acetic acid, and then 450 mL of fuming nitric acid (d=1.50) were dropped to the mixture. The reaction solution was stirred at room temperature for 7 hours. The reaction solution was poured into 5 L of water, and then the precipitated crystal was separated by filtration and recovered. The resultant crystal was washed with water and methanol, and was then dried under reduced pressure. Thus, 280 g of an orange crystal were obtained (in 74% yield).

Workup

  1. customthe precipitated crystal was separated by filtration
  2. customrecovered
  3. washThe resultant crystal was washed with water and methanol
  4. customwas then dried under reduced pressure

Sources & evidence

ORD record
ord-c9da76e155e44659982615fddc8ae8b4
Source dataset
uspto-grants-2014_09
Patent number
US08822041B2

Reaction notes

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