Ethanol → Ethyl 3-nitrocinnamate

HRID 865875Notes

Reaction equation

HRID 865875 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[CH:7]=[CH:8][C:9]([OH:11])=[O:10])([O-:3])=[O:2].S(=O)(=O)(O)O.[CH2:20](O)[CH3:21]>>[N+:1]([C:4]1[CH:5]=[C:6](/[CH:7]=[CH:8]/[C:9]([O:11][CH2:20][CH3:21])=[O:10])[CH:12]=[CH:13][CH:14]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 683902-Propenoic acid, 3-(3-nitrophenyl)-

Product 1

HCID 5354248Ethyl 3-nitrocinnamateYield 99%

Procedure

A mixture of 3-nitrocinnamic acid (11.7 g, 60.6 mmol), concentrated sulfuric acid (0.16 mL, 3.03 mmol) and absolute ethanol (120 mL) was refluxed overnight. The reaction mixture was poured into ice water (400 mL). The mixture was extracted with ethyl ether (500 mL×2). The organic layer was washed with saturated sodium bicarbonate solution (100 mL×2), water (100 mL×2), brine (100 mL×2) and dried over magnesium sulfate. Evaporation gave title compound (12.0 g, 99%) as a colorless oil.

Workup

  1. temperaturewas refluxed overnight
  2. extractionThe mixture was extracted with ethyl ether (500 mL×2)
  3. washThe organic layer was washed with saturated sodium bicarbonate solution (100 mL×2), water (100 mL×2), brine (100 mL×2)
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation

Sources & evidence

ORD record
ord-d468b46e9e1e4f3ba1e3ab0a6701df62
Source dataset
uspto-grants-1996_10
Patent number
US05567841

Reaction notes

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