Formaldehyde → Ethyl alpha-(phenethyl)acrylate

HRID 983672Notes

Reaction equation

HRID 983672 reaction equation
C([C:3]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:7](O)=O)[C:4]([OH:6])=[O:5])C.N1CCC[CH2:20][CH2:19]1.C=O>>[CH2:7]=[C:3]([CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:4]([O:6][CH2:19][CH3:20])=[O:5]

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 8082PiperidineHCID 22561331Monoethyl 2-[2-(phenyl)ethyl]malonic acid

Product 1

HCID 11117162Ethyl alpha-(phenethyl)acrylateYield 89%

Conditions

Temperature
57.5 °C

Procedure

Monoethyl 2-[2-(phenyl)ethyl]malonic acid (47.2 g, 200 mole) was added to 40 mL round bottom flask fitted with a Teflon coated stirring bar. Piperidine (3 mL) and paraformaldehyde (8.4 g, 280 mmole) were added to the flask and the flask was heated to 55-60° C., until gas evolution ceased. TLC indicated that no starting material remained. The solution was worked up by removing the solvent under reduced pressure. Water (50 mL) and enough 12N HCl was added to the flask to acidify the mixture (pH>3). The mixture was extracted with ether (3×50 mL) and back extracted with brine. The solution was dried over MgSO4 and filtered. The reaction mixture was shown to be clean by NMR and TLC and used without further purification. Recovered 36.3 g material (89% yield).

Workup

  1. customfitted with a Teflon coated stirring bar
  2. customby removing the solvent under reduced pressure
  3. additionWater (50 mL) and enough 12N HCl was added to the flask
  4. extractionThe mixture was extracted with ether (3×50 mL)
  5. extractionback extracted with brine
  6. dry with materialThe solution was dried over MgSO4
  7. filtrationfiltered
  8. customused without further purification

Sources & evidence

ORD record
ord-8c2dc2657849450cbfd727c9ee3dd93c
Source dataset
uspto-grants-2005_03
Patent number
US06864383B2

Reaction notes

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