Benzene → 98272-33-4

Temperature

55 °C

To a suspension of 85.8 g of methoxycarbonylmethylenetriphenylphosphorane in 550 ml of benzene is added dropwise a solution of 15.0 g of cyclopropanecarbaldehyde in 50 ml of benzene at room temperature under argon atmosphere. The mixture is stirred at 55° C. overnight. After the reaction mixture is cooled to room temperature, the reaction mixture is poured into 800 ml of ice water. The aqueous mixture is extracted with 600 ml of chloroform twice. The chloroform layer is washed with brine. The organic layer is dried and evaporated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography (solvent; hexane:ethyl acetate=12:1) to give 17.4 g of methyl trans-3-cyclopropylacrylate.

1. temperatureAfter the reaction mixture is cooled to room temperature
2. extractionThe aqueous mixture is extracted with 600 ml of chloroform twice
3. washThe chloroform layer is washed with brine
4. customThe organic layer is dried
5. customevaporated under reduced pressure
6. customto remove the solvent
7. customThe residue is purified by silica gel column chromatography (solvent; hexane:ethyl acetate=12:1)

ORD record

ord-4705d529d72e44d9b45b2f416bd1122c

Source dataset

uspto-grants-1996_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05589502