Toluene → Propanoic acid, 3-chloro, 2-propenyl ester
Reaction equation
C([OH:4])C=C.[Cl:5][CH2:6][CH2:7][C:8](Cl)=[O:9].[C:11]1([CH3:17])C=CC=C[CH:12]=1>>[Cl:5][CH2:6][CH2:7][C:8]([O:9][CH2:17][CH:11]=[CH2:12])=[O:4]Participants
4
Procedure
58.08 g (1.0 mol) of allyl alcohol were dissolved in 200 ml of toluene, and 190.46 g (1.5 mol) of 3-chloropropionyl chloride were added dropwise at 90° C. The reaction solution was refluxed for a further 1.5 hours. The organic phase was washed with 10% strength NaOH solution and twice with H2O, and the solvent was evaporated. The product was subsequently distilled at 74° C. and 20 mbar, giving 104.3 g of allyl 3-chloropropionate (71% of theory).
Workup
- temperatureThe reaction solution was refluxed for a further 1.5 hours
- washThe organic phase was washed with 10% strength NaOH solution and twice with H2O
- customthe solvent was evaporated
- distillationThe product was subsequently distilled at 74° C.
Sources & evidence
- ORD record
- ord-7d0791f68dfe40f5907771d28b937502
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06486338B1
Reaction notes
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