Water → Phenyl pent-4-enoate

HRID 240235

Reaction equation

HRID 240235 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][CH2:3][CH:4]=[CH2:5].[O-:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Na+].O>C1COCC1>[C:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:6])[CH2:2][CH2:3][CH:4]=[CH2:5]

Participants

5

Reactant 3

HCID 962WaterHCID 42284934-Pentenoyl chlorideHCID 4445035Phenolate Sodium

Product 1

HCID 15255467Phenyl pent-4-enoateYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Pentenoyl chloride (8.16 g, 69.1 mmol) was added dropwise to sodium phenoxide (8.02 g, 69.1 mmol) in THF (160 ml) at 20° C. After 24 hours at 20° C. H2O (100 ml) was added and the aqueous phase was extracted with Et2O (3×200 ml). The organic phase was washed with NaHCO3 (2×200 ml), brine (2×200 ml) to neutrality, then dried (Na2SO4), filtered, concentrated and bulb-to-bulb distilled to afford the desired title ester in 90% yield. B.p.: 70° C./0.04 mbar.

Workup

  1. extractionthe aqueous phase was extracted with Et2O (3×200 ml)
  2. washThe organic phase was washed with NaHCO3 (2×200 ml), brine (2×200 ml) to neutrality
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. distillationbulb-to-bulb distilled

Sources & evidence

ORD record
ord-92761f81248546f4abca12ccb94eb3fb
Source dataset
uspto-grants-2014_02
Patent number
US08648032B2

Linked notes

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