Hydrochloric Acid → 2,4-Dinitro-1-(octadecyloxy)benzene

HRID 583538Notes

Reaction equation

HRID 583538 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[OH:13])([O-:3])=[O:2].[CH2:14](Br)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].C(=O)([O-])[O-].[Na+].[Na+].Cl>O.CN(C)C=O>[CH2:31]([O:13][C:5]1[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14932,4-DinitrophenolHCID 82181-BromooctadecaneHCID 10340Sodium Carbonate

Product 1

HCID 187981952,4-Dinitro-1-(octadecyloxy)benzeneYield 79.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,4-dinitrophenol (85 wt %, 6.72 g, 31 mmol), octadecyl bromide (20.7 g, 62 mmol), sodium carbonate (6.57 g, 62 mmol) and dimethylformamide (31 mL) was heated to 100° C. under a nitrogen atmosphere for 22 hrs. The cooled mixture was diluted with water (200 mL), acidified with 10 N hydrochloric acid (50 mL) and extracted with ether. The extracts were washed with water and brine, and dried over magnesium sulfate. The solvent was removed and the solid recrystallized to give 1-octadecyloxy-2,4- dinitrobenzene (10.7 g, 79%): mp 63.5-64.0° C.

Workup

  1. extractionextracted with ether
  2. washThe extracts were washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed
  5. customthe solid recrystallized

Sources & evidence

ORD record
ord-b277d4a093e34004afe20210d28e026e
Source dataset
uspto-grants-1999_07
Patent number
US05929201

Reaction notes

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