Benzaldehyde → 2-Oxo-4-phenylbut-3-enoic acid

HRID 1032040Notes

Reaction equation

HRID 1032040 reaction equation
[C:1]([O-:6])(=[O:5])[C:2]([CH3:4])=[O:3].[Na+].[CH:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl>[OH-].[Na+]>[CH:8](=[CH:4][C:2](=[O:3])[C:1]([OH:6])=[O:5])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 23662274Sodium pyruvate

Product 1

HCID 2434352-Oxo-4-phenylbut-3-enoic acidYield 75%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Sodium pyruvate (60.5 g, 0.55 mol) was first added to a cold (0° C.) 1N aqueous solution of sodium hydroxide (550 ml). Benzaldehyde (53 g, 0.55 mol) was then added at such a rate that the temperature was maintained below 5° C. The reaction mixture was then aged four hours at 0° C. with good agitation. Following the age period, the mixture was acidified to pH 1.0 with 6N HCl maintaining a temperature of 0°-5° C. After acidification, the benzalpyruvic acid product was extracted with 500 ml ethyl acetate. Yield: 75-77% by HPLC analysis. Anal. Calcd. for C10H7O3K: C, 56.08; H, 3.30; K, 18.21. Found: C, 56.11; H, 3.31; K, 18.20. 1H NMR (acetone-d6) δ: 7.2 (d, 1H), 7.8 (d, 1H), 7.5 (s, 5H). IR (KBr) cm-1 : 3500sb, 3050-2900s, 1740s, 1695s, 1230s, 1020s.

Workup

  1. temperaturewas maintained below 5° C
  2. customa temperature of 0°-5° C
  3. extractionAfter acidification, the benzalpyruvic acid product was extracted with 500 ml ethyl acetate

Sources & evidence

ORD record
ord-790204792e504a828095b7d3f2818756
Source dataset
uspto-grants-1990_09
Patent number
US04956490

Reaction notes

Loading…