Methanol → Hexyl 4,4-dinitropentanoate

HRID 573472

Reaction equation

HRID 573472 reaction equation
[N+:1]([CH:4]([N+:6]([O-:8])=[O:7])[CH3:5])([O-:3])=[O:2].[OH-].[K+].[C:11]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])(=[O:14])[CH:12]=[CH2:13].CO>O>[N+:1]([C:4]([N+:6]([O-:8])=[O:7])([CH3:5])[CH2:13][CH2:12][C:11]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:14])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 17259Hexyl acrylateHCID 611501,1-Dinitroethane

Product 1

HCID 86717671Hexyl 4,4-dinitropentanoateYield 81.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Dinitroethane (2.4 g, 0.02 mol) and potassium hydroxide (1.2 g, 0.022 mol) were dissolved in 50 mL of water to form a first solution. 50 mL of water was added to the first solution to dissolve a salt remaining in the first solution to form a second solution. Hexyl acrylate (8.8 mL, 0.05 mol) was mixed with 50 mL of methanol, and then the mixture was slowly added to the second solution to form a third solution. The third solution was stirred at room temperature for 4 hours. The reaction product was extracted by diethyl ether, and was then distilled under reduced pressure to obtain yellow liquid hexyl 4,4-dinitropentanoate (4.5 g, yield: 81%).

Workup

  1. customto form a first solution
  2. dissolutionto dissolve a salt
  3. customto form a second solution
  4. additionthe mixture was slowly added to the second solution
  5. customto form a third solution
  6. extractionThe reaction product was extracted by diethyl ether
  7. distillationwas then distilled under reduced pressure

Sources & evidence

ORD record
ord-2553d52d7ccd47b69a8bf6802b9b1d56
Source dataset
uspto-grants-2015_05
Patent number
US09029591B2

Linked notes

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