Hydrochloric Acid → 4-Allyloxy-3-nitrocinnamic acid

HRID 260307

Reaction equation

HRID 260307 reaction equation
[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][C:6]=1[N+:13]([O-:15])=[O:14])[CH:2]=[CH2:3].C(O)(=O)[CH2:17][C:18]([OH:20])=[O:19].N1CCCCC1.Cl>N1C=CC=CC=1>[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH:17][C:18]([OH:20])=[O:19])=[CH:7][C:6]=1[N+:13]([O-:15])=[O:14])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 224011524-Allyloxy-3-nitrobenzaldehyde

Product 1

HCID 543811174-Allyloxy-3-nitrocinnamic acidYield 70.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Allyloxy-3-nitrobenzaldehyde (5 g, 24.1 mM) was dissolved in pyridine (100 ml) and malonic acid (5.02 g, 48.3 mM) and piperidine (0.48 ml, 4.8 mM) added. The mixture was heated to reflux with stirring for 2 hours, cooled, and poured onto a mixture of concentrated hydrochloric acid and ice. Organics were extracted into ethyl acetate, the organic layer washed with 2M hydrochloric acid, and product back-extracted into aqueous NaHCO3. The aqueous solution was then re-acidified (concentrated hydrochloric acid), and organics extracted into ethyl acetate, washed with brine, and dried (MgSO4), to give title compound (4.23 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperaturecooled
  4. extractionOrganics were extracted into ethyl acetate
  5. washthe organic layer washed with 2M hydrochloric acid, and product
  6. extractionback-extracted into aqueous NaHCO3
  7. extractionre-acidified (concentrated hydrochloric acid), and organics extracted into ethyl acetate
  8. washwashed with brine
  9. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-2d00ecb238134095b6b0426401ec41a6
Source dataset
uspto-grants-1996_06
Patent number
US05527791

Linked notes

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