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

HRID 2932

Reaction equation

HRID 2932 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 h. The cooled mixture was diluted with water (200 mL), acidified with 10N 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-ef6ff2ed718b4bfdb1e48398ec37733b
Source dataset
uspto-grants-1998_03
Patent number
US05731405

Linked notes

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