Pyruvic Acid → HCID 74088930, compound

HRID 2266767Notes

Reaction equation

HRID 2266767 reaction equation
[CH:1](=O)/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:11]([OH:16])(=[O:15])[C:12]([CH3:14])=[O:13].[OH-].[K+:18]>CO>[O:13]=[C:12]([CH:14]=[CH:1][CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:11]([O-:16])=[O:15].[K+:18]

Participants

5

Reactant 3

HCID 1060Pyruvic AcidHCID 14797Potassium Hydroxide2×HCID 637511Cinnamaldehyde

Product 1

HCID 74088930HCID 74088930, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
2.5 °C

Procedure

A solution of trans-cinnamaldehyde (26.43 g) and pyruvic acid (11.9 mL) in 10 mL of methanol was stirred and chilled to 0-5° C. in an ice bath. To the chilled solution was added 35 nL of potassium hydroxide (16.83 g in 50 mL of methanol) over a period of 20 minutes. The remaining methanolic potassium hydroxide was added rapidly and the ice bath was removed. The solution changed from a yellow to a dark orange and the precipitate was formed. The reaction mixture was chilled in the refrigerator overnight and the solid was collected by filtration, washed with 50 mL of methanol three times, 50 mL of ether and then air dried to afford 29.3 g of the desired 2-oxo-6-phenyl-3,5-hexadienoate as a yellow solid (61.0%). 1H NMR (DMSO-d6/D2O, 300 MHz), δ(ppm) 7.48 (d, 2H), 7.28 (m, 4H), 7.12 (d, 2H), 6.27 (d, 1H).

Workup

  1. customthe ice bath was removed
  2. customwas formed
  3. temperatureThe reaction mixture was chilled in the refrigerator overnight
  4. filtrationthe solid was collected by filtration
  5. washwashed with 50 mL of methanol three times, 50 mL of ether
  6. customair dried

Sources & evidence

ORD record
ord-b941a5c7abc449b184b53714dbbcd6dc
Source dataset
uspto-grants-2010_12
Patent number
US07858664B2

Reaction notes

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