Nitric Acid → 2-Nitro-4-(5-dodecylpyrimidine-2-yl)phenol

HRID 1612599Notes

Reaction equation

HRID 1612599 reaction equation
[CH2:1]([C:13]1[CH:14]=[N:15][C:16]([C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)=[N:17][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[N+:26]([O-])([OH:28])=[O:27].O>S(=O)(=O)(O)O>[N+:26]([C:21]1[CH:20]=[C:19]([C:16]2[N:17]=[CH:18][C:13]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:14][N:15]=2)[CH:24]=[CH:23][C:22]=1[OH:25])([O-:28])=[O:27]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 1360357064-(5-Dodecyl-2-pyrimidinyl)phenol

Product 1

HCID 1357606302-Nitro-4-(5-dodecylpyrimidine-2-yl)phenolYield 81.7%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Step i) 2.00 g (5.87 mM) of 4-(5-dodecylpyrimidine-2-yl)phenol was dispersed in 20 ml of conc. sulfuric acid. To the dispersion, 0.50 ml of nitric acid (60%, density=1.38) was gradually added dropwise under cooling and stirring at 2°-8° C. After the addition, the mixture was stirred for 30 min. at about 5° C. After the reaction, the reaction mixture was poured into 150 ml of iced water to precipitate a crystal. The crystal was recovered by filtration, washed with water and recrystallized from ethanol to obtain 1.85 g of 2-nitro-4-(5-dodecylpyrimidine-2-yl)phenol (yield:81.7%).

Workup

  1. temperatureunder cooling
  2. additionAfter the addition
  3. stirringthe mixture was stirred for 30 min. at about 5° C
  4. customAfter the reaction
  5. customto precipitate a crystal
  6. filtrationThe crystal was recovered by filtration
  7. washwashed with water
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-2e6b134deebc4ad882d74ae76f2936dc
Source dataset
uspto-grants-1993_03
Patent number
US05190690

Reaction notes

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