Acrylic Acid → HCID 131734706, compound

HRID 1773127Notes

Reaction equation

HRID 1773127 reaction equation
[C:1]([O:4][C:5]1[CH:12]=[CH:11][C:10](I)=[CH:9][C:6]=1[CH:7]=[O:8])(=[O:3])[CH3:2].C(N(CC)CC)C.[C:21]([OH:25])(=[O:24])[CH:22]=[CH2:23].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:7]([C:6]1[CH:9]=[C:10]([CH:11]=[CH:12][C:5]=1[O:4][C:1](=[O:3])[CH3:2])[CH:23]=[CH:22][C:21]([OH:25])=[O:24])=[O:8]

Participants

7

Reactant 4

HCID 6581Acrylic AcidHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 89690163HCID 89690163, compound

Product 1

HCID 131734706HCID 131734706, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
67.5 °C

Procedure

2-Acetyloxy-5-iodobenzaldehyde (0.2 g, 0.69 mmol) is dissolved in 25 ml of acetonitrile and oxygen is removed by bubbling nitrogen through the solution. Triethylamine (0.673 ml, 4.82 mmol) and acrylic acid (0.095 ml, 1.38 mmol) are added dropwise with stirring, followed by 0.016 g of tri-o-tolylphosphine (0.069 mmol) and 0.008 of palladium(II) acetate (0.047 mmol). The mixture is heated at 65-70° C. for 4 hours, volatiles are removed by distillation and the residue is purified by column chromatography on silica gel, eluting with mixtures of ethyl acetate-hexane of increasing polarity. 3-Formyl-4-acetyloxycinnamic acid (0.095 g) is obtained as a white solid.

Workup

  1. customoxygen is removed
  2. customby bubbling nitrogen through the solution
  3. customvolatiles are removed by distillation
  4. customthe residue is purified by column chromatography on silica gel
  5. washeluting with mixtures of ethyl acetate-hexane
  6. temperatureof increasing polarity

Sources & evidence

ORD record
ord-5390f510b97446bf9fdb0bed01d6f9b5
Source dataset
uspto-grants-2016_02
Patent number
US09255071B2

Reaction notes

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