Formaldehyde → Ethyl 2-phenylacrylate

HRID 1635684Notes

Reaction equation

HRID 1635684 reaction equation
[C:1]1([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13](=O)([O-])[O-].[K+].[K+].C=O.O>CN1CCCC1=O>[C:8]([O:10][CH2:11][CH3:12])(=[O:9])[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[CH2:13]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 7590Ethyl phenylacetateHCID 11430Potassium Carbonate

Product 1

HCID 89651Ethyl 2-phenylacrylateYield 53.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

94 g of ethyl phenylacetate (methyl ester content 0.01%) were stirred in 300 ml of N-methylpyrrolidone with 120 g of potassium carbonate and 25 g of paraformaldehyde at 75 to 80° C. for 1.5 h. After cooling, 150 ml of water were added, and the aqueous phase was separated off. The N-methylpyrrolidone phase was extracted twice with 75 ml of diisopropyl ether each time. The combined diisopropyl ether phases were washed with 50 ml of water and concentrated in vacuo. 58 g of product were obtained, corresponding to 54 g of ethyl atropate (53% of theory) with a methyl atropate content of 0.03%.

Workup

  1. temperatureAfter cooling
  2. customthe aqueous phase was separated off
  3. extractionThe N-methylpyrrolidone phase was extracted twice with 75 ml of diisopropyl ether each time
  4. washThe combined diisopropyl ether phases were washed with 50 ml of water
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8171802f09684482b2a951bf5ffdc6bb
Source dataset
uspto-grants-2003_01
Patent number
US06509493B1

Reaction notes

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