Reacción #1519096

ord-b3f84c243fdf4899ad8fb80b2b1e2d41

Ecuación de reacción

O
water
O=Cc1ccc(Br)cc1
4-Bromobenzaldehyde
Cc1ccc(S(=O)(=O)O)cc1.O
p-toluenesulfonic acid monohydrate
OCCO
ethylene glycol
Brc1ccc(C2OCCO2)cc1
2-(4-bromophenyl)-1,3-dioxolane

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    LavadoThis solution was washed twice with aqueous bicarbonate
  2. 2
    Secadodried over magnesium sulfate
  3. 3
    Concentraciónconcentrated under reduced pressure
  4. 4
    OtroA colorless oil was recovered

Procedimiento

4-Bromobenzaldehyde (3 g, 0.0162 moles) in benzene (60 mL) was treated with p-toluenesulfonic acid monohydrate (0.15 g, 0.79 mmoles) and ethylene glycol (5 mL, 0.0896 moles). The reaction was refluxed under nitrogen with azeotropic removal of water. After 3 hours, the reaction was cooled to room temperature and diluted with an equal volume of ethyl acetate. This solution was washed twice with aqueous bicarbonate, dried over magnesium sulfate and concentrated under reduced pressure. A colorless oil was recovered. Yield=2.83 g (92%). TLC (5% ethyl acetate in hexanes) showed clean product, Rf=0.17.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07611909B1uspto-grants-2009_11