Water → HCID 54135884, compound

HRID 1956165Notes

Reaction equation

HRID 1956165 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)[CH3:4].[OH2:13].[O:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1>>[CH2:3]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH:16][C:15]([O:14][CH2:18][CH3:17])=[O:13])=[CH:7][CH:6]=1)[CH3:4]

Participants

5

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran3×HCID 208614-EthylbenzaldehydeHCID 24758Sodium hydride

Product 1

HCID 54135884HCID 54135884, compound

Procedure

A solution of 33.6 g of triethylphosphonoacetate in 20 mL of tetrahydrofuran was added dropwise with stirring to a slurry of 6.0 g of 60 percent sodium hydride (in mineral oil) in 100 ml of dry tetrahydrofuran. The mixture was allowed to react for 30 min and then a solution of 20.1 g of 4-ethylbenzaldehyde in 100 mL of tetrahydrofuran was added with stirring and the mixture was heated to reflux. After 2 hours the mixture was cooled and water was added. The resulting mixture was extracted with ethyl acetate and the extract was dried over sodium sulfate and concentrated by evaporation under reduced pressure to obtain ethyl 4-ethylcinnamate as the residue.

Workup

  1. customto react for 30 min
  2. temperaturethe mixture was heated to reflux
  3. temperatureAfter 2 hours the mixture was cooled
  4. extractionThe resulting mixture was extracted with ethyl acetate
  5. dry with materialthe extract was dried over sodium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-150d04572fb042c3bafeab62f2d651a9
Source dataset
uspto-grants-1998_07
Patent number
US05780465

Reaction notes

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