Water → Phenyl pent-4-enoate
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
Product 1
Reagents, catalysts & solvents 1
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
- extractionthe aqueous phase was extracted with Et2O (3×200 ml)
- washThe organic phase was washed with NaHCO3 (2×200 ml), brine (2×200 ml) to neutrality
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- distillationbulb-to-bulb distilled
Sources & evidence
- ORD record
- ord-92761f81248546f4abca12ccb94eb3fb
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08648032B2
Reaction notes
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