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Methanol → Octyl 4,4-dinitropentanoate

HRID 573474
Notes
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Reaction equation

HRID 573474 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][CH2:21][CH2:22][CH3:23])(=[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][CH2:21][CH2:22][CH3:23])=[O:14])([O-:3])=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 17258Octyl acrylateHCID 611501,1-Dinitroethane

Product 1

HCID 86717673Octyl 4,4-dinitropentanoateYield 82.1%

Reagents, catalysts & solvents 1

HCID 962Water
Solvent
2×

Procedure

Dinitroethane (2.4 g, 0.02 mol) and potassium hydroxide (1.2 g, 0.22 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. Octyl acrylate (10.2 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 octyl 4,4-dinitropentanoate (5.0 g, yield: 82%).

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-f9fd0aed86fe4aeb8956fc0eb5ca07d9
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09029591B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes