Nitroethane → HCID 66801851, compound

HRID 1843933Notes

Reaction equation

HRID 1843933 reaction equation
[N+:1]([CH2:4][CH3:5])([O-:3])=[O:2].[F:6][C:7]([F:17])([F:16])[C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1.C([O-])(=O)C.[NH4+].C(OC(=O)C)C>CCCCCC>[N+:1]([C:4]([CH3:5])=[CH:12][C:11]1[CH:14]=[CH:15][C:8]([C:7]([F:17])([F:16])[F:6])=[CH:9][CH:10]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6587NitroethaneHCID 8857Ethyl AcetateHCID 679964-(Trifluoromethyl)benzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 66801851HCID 66801851, compoundYield 42.93%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
115 °C

Procedure

Nitro ethane (30.94 mL, 430.73 mmol) was added to 4-trifluoromethyl-benzaldehyde (5 g, 28.71 mmol) and ammonium acetate (6.64 g, 86.15 mmol) and the resulting mixture was refluxed at 115° C. overnight. The reaction was monitored by TLC (10% ethylacetate in hexane). The reaction mass was cooled and partitioned between ethylacetate and water. The organic layer was washed with water, brine solution, dried over anhydrous sodium sulphate and concentrated. Purification by column chromatography on silica gel (2% ethylacetate in hexane) afforded 2.85 g of the product (42.93% yield).

Workup

  1. temperatureThe reaction mass was cooled
  2. custompartitioned between ethylacetate and water
  3. washThe organic layer was washed with water, brine solution
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated
  6. customPurification by column chromatography on silica gel (2% ethylacetate in hexane)

Sources & evidence

ORD record
ord-da3f868b19fa48a6b333640eaa2fde44
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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