Hydrochloric Acid → Anthracene, 2-methyl-9-nitro-

HRID 1859210Notes

Reaction equation

HRID 1859210 reaction equation
[CH3:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[CH:5][C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1.[N+:16]([O-])([OH:18])=[O:17].Cl>C(O)(=O)C>[CH3:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([N+:16]([O-:18])=[O:17])[C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 944Nitric AcidHCID 119362-Methylanthracene

Product 1

HCID 190418Anthracene, 2-methyl-9-nitro-

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
22.5 °C

Procedure

Synthesis of 2-methyl-9-nitroanthracene ##STR12## Nitration of 2-methylanthracene (Source Aldrich) was carried out using the same procedure as in example 1 to yield the 2-methyl-9-nitroanthracene as a yellow solid. 2-Methylanthracene (2.0 g; 0.010 mole) was suspended in glacial acetic acid (25 ml) and to the stirred solution was added concentrated nitric acid (0.6 ml; 0.014 mole). The solution was stirred in a water bath at 20-25° C. for 4 hours, until the solution became clear. To the clear solution a mixture of conc. HCl and acetic acid (20 ml; 1:1) was added via a dropping funnel over a period of 15 minutes. A yellow solid precipitated out. The solution was stirred for further 30 minutes and filtered under suction. The product was treated by the same method as described in example 1 to give the 2-methyl-9-nitroanthracene as a yellow solid (1.8 g; 73%).

Workup

  1. additionwas added via a dropping funnel over a period of 15 minutes
  2. customA yellow solid precipitated out
  3. stirringThe solution was stirred for further 30 minutes
  4. filtrationfiltered under suction
  5. additionThe product was treated by the same method

Sources & evidence

ORD record
ord-4967da2f40f3471c8afe5f2ef247bcf9
Source dataset
uspto-grants-2000_11
Patent number
US06153726

Reaction notes

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