Pyruvic Acid → HCID 74088930, compound

HRID 1967075Notes

Reaction equation

HRID 1967075 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 mL 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-c52832e9af83435eaa5bfd66dd878265
Source dataset
uspto-grants-2013_04
Patent number
US08420698B2

Reaction notes

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