Nitromethane → HCID 85527109, compound

HRID 330102Notes

Reaction equation

HRID 330102 reaction equation
[N+:1]([CH3:4])([O-:3])=[O:2].C[O-].[Na+].[Na].[O:9]=[C:10]([CH:22]=[CH2:23])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19]>C(OC(=O)C)C.CO>[O:9]=[C:10]([CH2:22][CH2:23][CH2:4][N+:1]([O-:3])=[O:2])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19]

Participants

7

Reactant 4

HCID 6375NitromethaneHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 1112758610-Undecenoic acid, 9-oxo-, methyl ester

Product 1

HCID 85527109HCID 85527109, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-20 °C

Procedure

Nitromethane (10.6 g) is added dropwise to a solution at 0°-5° C. of sodium methoxide prepared from sodium (3.8 g; 0.2 mole) and methanol (165 ml). Ethylacetate (165 ml) is added. The solution is cooled to -20° C. and, in 1 hour, the methyl ester (III) (17.5 g) is added dropwise. The mixture is stirred at -20° C. for 15 minutes and then poured into water/ice. The phases are separated and extracted with ethyl acetate to obtain a thick oil (16.5 g; yield=73%) which is crystallized with pentane to yield the ester (IV).

Workup

  1. customThe phases are separated
  2. extractionextracted with ethyl acetate
  3. customto obtain a thick oil (16.5 g; yield=73%) which
  4. customis crystallized with pentane

Sources & evidence

ORD record
ord-36cf1bd59f154d92938bce908a5f5a3f
Source dataset
uspto-grants-1990_01
Patent number
US04894473

Reaction notes

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