Reacción #42772

ord-a542f2d9ff694a16a34c015a0ccdb19f

Ecuación de reacción

CC(=O)[O-].[Na+]
sodium acetate
Oc1cccc(O)c1
resorcinol
O=C(O)Cc1ccc(Cl)cc1
4-chlorophenylacetic acid
CCOCC.FB(F)F
boron trifluoride etherate
O=C(Cc1ccc(Cl)cc1)c1ccc(O)cc1O
title compound
O=C(Cc1ccc(Cl)cc1)c1ccc(O)cc1O
2-(4-Chlorophenyl)-1-(2,4-dihydroxyphenyl)-ethanone

Condiciones de reacción

Temperatura
85°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturato cool to room temperature
  2. 2
    workup.STIRRINGThe suspension is stirred overnight at room temperature
  3. 3
    OtroThe orange brown precipitate is removed by filtration
  4. 4
    Otrodried in vacuo
  5. 5
    Otrotriturated with isopropyl ether/hexane (1:9)
  6. 6
    Otroto give a yellow solid
  7. 7
    LavadoThis solid is washed with hexane
  8. 8
    Otrodried in vacuo

Procedimiento

A mixture of resorcinol (100 g, 0.908 mol), 4-chlorophenylacetic acid (170 g, 0.999 mol) and boron trifluoride etherate is stirred mechanically at 85° C. for 1.75 h. The dark red-brown reaction mixture is allowed to cool to room temperature and then poured slowly into aqueous sodium acetate (1 l, 30% w/v). The suspension is stirred overnight at room temperature. The orange brown precipitate is removed by filtration, dried in vacuo and then triturated with isopropyl ether/hexane (1:9) to give a yellow solid. This solid is washed with hexane and dried in vacuo to provide the title compound. A further three crops of material are obtained from the sodium acetate work-up mixture.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07732435B2uspto-grants-2010_06