Formaldehyde → Ethyl 2-benzylacrylate

HRID 1978212Notes

Reaction equation

HRID 1978212 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH:5]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:6](O)=O)[CH3:2].N1CCCCC1.C=O>N1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:16])[C:5]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[CH2:6])[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8082PiperidineHCID 28848672-Benzyl-malonic acid monoethyl ester

Product 1

HCID 11084648Ethyl 2-benzylacrylateYield 84.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
130 °C

Procedure

Benzylmalonic acid monoethyl ester (8.0 g, 36 mmol), 7 mL of pyridine, 0.36 mL (3.6 mmol) of piperidine, and 1.06 g (35 mmol) of paraformaldehyde is refluxed under nitrogen for 1.5 hours in an oil bath maintained at 130° C. After cooling for 0.5 hours the mixture is partitioned between 100 mL of water and 100 mL of hexane. The aqueous phase is re-extracted with 50 mL of hexane. The organic phase is washed with aqueous 10% HCl, water, 1M sodium bicarbonate, and brine. It is dried over anhydrous sodium sulfate and concentrated in vacuo, yielding 5.8 g of the title compound as a colorless oil.

Workup

  1. temperatureAfter cooling for 0.5 hours the mixture
  2. customis partitioned between 100 mL of water and 100 mL of hexane
  3. extractionThe aqueous phase is re-extracted with 50 mL of hexane
  4. washThe organic phase is washed with aqueous 10% HCl, water, 1M sodium bicarbonate, and brine
  5. dry with materialIt is dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f4a570f9e5374018931c172ecdad722f
Source dataset
uspto-grants-2001_05
Patent number
US06235928B1

Reaction notes

Loading…