Acetic Acid → HCID 4198600, compound

HRID 636730Notes

Reaction equation

HRID 636730 reaction equation
[CH:1](=O)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:11][C:12]([N+:15]([O-])=[O:16])([CH3:14])[CH3:13].C(O)(=O)C>C(O)C.[Zn]>[C:4]1([CH:3]=[CH:2][CH:1]=[N+:15]([C:12]([CH3:14])([CH3:13])[CH3:11])[O-:16])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 3073-Phenylprop-2-EnalHCID 116722-Methyl-2-nitropropane

Product 1

HCID 4198600HCID 4198600, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

To a suspension of cinnamaldehyde (769.8 mg, 5.82 mmol), 1,1-dimethylnitroethane (1.20 g, 11.6 mmol) and zinc (1.14 g, 17.4 mmol) in ethanol (30 ml) was added acetic acid (2.10 g, 35.0 mmol) dropwise at 5° C. while stirring. The mixture was stirred at room temperature for 3 hours and let stand for 6 days. After cooling the mixture to 5° C., zinc acetate was filtered off and the filtrate was concentrated and purified by silica gel chromatography (hexane/ethyl acetate=1/1-0/1).

Workup

  1. stirringThe mixture was stirred at room temperature for 3 hours
  2. filtrationzinc acetate was filtered off
  3. concentrationthe filtrate was concentrated
  4. custompurified by silica gel chromatography (hexane/ethyl acetate=1/1-0/1)

Sources & evidence

ORD record
ord-bfa2036262bd4de6aa6a8e4cba4afb29
Source dataset
uspto-grants-2001_02
Patent number
US06194461B1

Reaction notes

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