Reaktion #3707

ord-1b59e09c326a4a03910529e081276b80

Reaktionsgleichung

COC(=O)c1ccc(CC(=O)c2ccccc2Cl)cc1
methyl 4-[2-(2-chlorophenyl)-2-oxoethyl]benzoate
[Na+].[OH-]
NaOH
O=C(O)CC(O)(CC(=O)O)C(=O)O
citric acid
O=C(O)c1ccc(CC(=O)c2ccccc2Cl)cc1
desired product
Ausbeute 96.7%
O=C(O)c1ccc(CC(=O)c2ccccc2Cl)cc1
4-[2-(2-Chlorophenyl)-2-oxoethyl]benzoic acid
Ausbeute 96.7%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturis refluxed for 3 hours
  2. 2
    SonstigeThe reaction mixture is evaporated in vacuo
  3. 3
    Sonstigeto remove the CH3OH
  4. 4
    ExtraktionThe aqueous phase is extracted with CH2Cl2
  5. 5
    SonstigeThe resulting solid is collected
  6. 6
    Sonstigedried under vacuum

Vorschrift

A mixture of 18.78 g of methyl 4-[2-(2-chlorophenyl)-2-oxoethyl]benzoate in 288.8 ml of CH3OH, 72.2 ml of water and 5.2 g of NaOH is refluxed for 3 hours then acidified with 2N citric acid. The reaction mixture is evaporated in vacuo to remove the CH3OH. The aqueous phase is extracted with CH2Cl2 and acidified with 1N HCl. The resulting solid is collected and dried under vacuum to give 17.27 g of the desired product, m.p. 168°-172° C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05733905uspto-grants-1998_03