Pyridine → 2-Propenoic acid, 2-(benzoyloxy)-, ethyl ester

HRID 1766430Notes

Reaction equation

HRID 1766430 reaction equation
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])[C:2]([CH3:4])=[O:3].N1C=CC=CC=1.[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])O.[Na+]>C(OCC)C>[C:15]([O:3][C:2](=[CH2:4])[C:1]([O:6][CH2:7][CH3:8])=[O:5])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 12041Ethyl pyruvate2×HCID 516892Sodium Bicarbonate

Product 1

HCID 117907062-Propenoic acid, 2-(benzoyloxy)-, ethyl esterYield 54.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

While ethyl pyruvate (174 g, 1.5 mol) was being stirred at 0° C., pyridine (120 g, 1.5 mol) was dropped into the ethyl pyruvate. After it was stirred at 0° C. for 10 minutes, benzoyl chloride (210 g, 1.5 mol) was slowly dropped into this mixture. After the temperature of the reaction solution reached room temperature, the reaction solution was stirred for 48 hours. An aqueous solution of saturated sodium hydrogencarbonate and diethyl ether were added to the reaction solution, and an organic layer was separated by use of a separating funnel. Diethyl ether was again added to the aqueous layer and an organic compound was extracted. The obtained organic layer was then mixed with the organic compound, and sodium sulfate was added for dehydration. Thereafter, the sodium sulfate was removed by filtration and the solvent was removed by use of an evaporator under a reduced pressure. The concentrate was distilled under a reduced pressure (1 mmHg, 92 to 102° C.) to give ethyl α-benzoyloxyacrylate (180 g, yield: 54%).

Workup

  1. customreached room temperature
  2. stirringthe reaction solution was stirred for 48 hours
  3. customan organic layer was separated by use of a separating funnel
  4. additionDiethyl ether was again added to the aqueous layer
  5. extractionan organic compound was extracted
  6. additionThe obtained organic layer was then mixed with the organic compound, and sodium sulfate
  7. additionwas added for dehydration
  8. customThereafter, the sodium sulfate was removed by filtration
  9. customthe solvent was removed by use of an evaporator under a reduced pressure
  10. distillationThe concentrate was distilled under a reduced pressure (1 mmHg, 92 to 102° C.)

Sources & evidence

ORD record
ord-e0c0c0550e5a4ec3810c517f09b0655e
Source dataset
uspto-grants-2007_06
Patent number
US07230062B2

Reaction notes

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