Hydrochloric Acid → HCID 53411291, compound

HRID 2120318Notes

Reaction equation

HRID 2120318 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[CH:7]=[CH:8][C:9](O)=[O:10])([O-:3])=[O:2].C(OCC)(=O)C.S(Cl)([Cl:23])=O.Cl>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[CH:7]=[CH:8][C:9]([Cl:23])=[O:10])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 683902-Propenoic acid, 3-(3-nitrophenyl)-

Product 1

HCID 53411291HCID 53411291, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

193.2 g (1 mole) of 3-nitrocinnamic acid and 650 g of ethyl acetate were placed in a reaction vessel. While 200 g of thionyl chloride with some drops of DMF was dropped into the reaction mixtures, the reaction mixtures were refluxed with stirring until the generation of hydrogen chloride gas stopped. The reacted solution was concentrated until a solid could be precipitated and poured into hexane. The precipitate was separated by filtration and dried. 205 g of 3-nitrocinnamoyl chloride was yielded.

Workup

  1. customthe reaction mixtures
  2. temperaturewere refluxed
  3. concentrationThe reacted solution was concentrated until a solid
  4. customcould be precipitated
  5. additionpoured into hexane
  6. customThe precipitate was separated by filtration
  7. customdried

Sources & evidence

ORD record
ord-f5d754fe2faa4daa94a93368bb112a8c
Source dataset
uspto-grants-2004_02
Patent number
US06689899B2

Reaction notes

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