Pyruvic Acid → Potassium 2-oxo-8-phenyl-3,5,7-octatrienoate

HRID 970779Notes

Reaction equation

HRID 970779 reaction equation
[C:1]1([CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13]([OH:18])(=[O:17])[C:14]([CH3:16])=[O:15].[OH-].[K+:20]>CO>[O:15]=[C:14]([CH:16]=[CH:11][CH:10]=[CH:9][CH:8]=[CH:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:13]([O-:18])=[O:17].[K+:20]

Participants

5

Reactant 3

HCID 1060Pyruvic AcidHCID 14797Potassium Hydroxide2×HCID 1146512,4-Pentadienal, 5-phenyl-

Product 1

HCID 74088932Potassium 2-oxo-8-phenyl-3,5,7-octatrienoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 5-phenyl-2,4-pentadienal (6.70 g) and pyruvic acid (3.0 mL) in 5 mL of methanol was stirred and chilled to 0–5° C. in an ice bath. To the chilled solution was added a solution of 35 mL of potassium hydroxide (3.5 g) in 10 mL of methanol dropwise over a period of 30 minutes. The remaining methanolic potassium hydroxide was added rapidly and the ice bath was removed. The reaction was allowed to warm to room temperature and stirred for another hour. The flask was then refrigerated overnight. The solid was collected by filtration, washed with 15 mL of methanol three times, 15 mL of ether and then air dried to afford 6.69 g of potassium 2-oxo-8-phenyl-3,5,7-octatrienoate as a yellow solid. 1H NMR (DMSO-d6, 300 MHz), δ(ppm) 7.52 (d, 2H), 7.32 (m, 3H), 7.10 (m, 2H), 6.83 (dd, 2H), 6.57 (dd, 1H), 6.13 (d, 1H).

Workup

  1. temperaturechilled to 0–5° C. in an ice bath
  2. customthe ice bath was removed
  3. customrefrigerated overnight
  4. filtrationThe solid was collected by filtration
  5. washwashed with 15 mL of methanol three times, 15 mL of ether
  6. customair dried

Sources & evidence

ORD record
ord-3fb45102d62143978fb3419800870be7
Source dataset
uspto-grants-2007_12
Patent number
US07312247B2

Reaction notes

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