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

HRID 601085Notes

Reaction equation

HRID 601085 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×

Conditions

Temperature
2.5 °C

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. customthe ice bath was removed
  2. temperatureto warm to room temperature
  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-521f270cedee461581eef88507702ba8
Source dataset
uspto-grants-2011_03
Patent number
US07902259B2

Reaction notes

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