Pyruvic Acid → HCID 131735956, compound

HRID 2207924Notes

Reaction equation

HRID 2207924 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]=O)=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:2].[C:18]([OH:23])(=[O:22])[C:19]([CH3:21])=[O:20].[OH-].[K+]>CO>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[CH:12][C:13]([CH:16]=[CH:21][C:19](=[O:20])[C:18]([OH:23])=[O:22])=[CH:14][CH:15]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 1060Pyruvic AcidHCID 14797Potassium HydroxideHCID 71742910HCID 71742910, compound

Product 1

HCID 131735956HCID 131735956, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a mixture of 3′-ethoxy-biphenyl-4-carbaldehyde (4.6 g, 20.1 mmol) prepared in Step 1 and pyruvic acid (1.7 mL, 24.1 mmol) in methanol (15.0 mL), was slowly added a solution of potassium hydroxide (2.0 g, 36.2 mmol) in methanol (15.0 mL) at 0° C. The reaction mixture was stirred at room temperature for 7 hours and then filtered. The resulting solid was diluted with a 1N hydrochloric acid solution and then extracted with ethyl acetate. The extract was washed with distilled water and brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give 2.5 g of the titled compound as a brown liquid.

Workup

  1. filtrationfiltered
  2. additionThe resulting solid was diluted with a 1N hydrochloric acid solution
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with distilled water and brine
  5. dry with materialdried on anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c75d488412104e82a7f38864788d74a1
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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