Reacción #444013

Ecuación de reacción

KOH

2-phenylbenzyl bromide

diethyl ethylmalonate

sodium

→

13

Rendimiento 93.0%

(±)-2-(2-phenylbenzyl)butyric acid

Rendimiento 93.0%

Disolventes

H2O

H2O

H2O

H2O

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was refluxed for 3 hours
2. 2
   workup.ADDITIONwere added at room temperature
3. 3
   Temperaturathe mixture was refluxed for a further 4 hours
4. 4
   OtroThe solvent was removed in vacuo, H2O
5. 5
   workup.ADDITIONwas added to the residue until the latter
6. 6
   workup.DISSOLUTIONhad dissolved completely
7. 7
   OtroThe precipitate which formed
8. 8
   Filtraciónwas filtered off with suction
9. 9
   Otrodried

Procedimiento

188 g (1 mol) of diethyl ethylmalonate dissolved in 100 cm3 of H2O-free EtOH are added dropwise at room temperature to 23 g (1 mol) of sodium in 400 cm3 of H2O-free EtOH. 247 g (1 mol) of 2-phenylbenzyl bromide in 300 cm3 of H2O-free EtOH were subsequently added dropwise, and the mixture was refluxed for 3 hours. 170 g (3 mol) of KOH dissolved in 300 cm3 of H2O were added at room temperature, and the mixture was refluxed for a further 4 hours. The solvent was removed in vacuo, H2O was added to the residue until the latter had dissolved completely, and the mixture was subsequently acidified to pH 1 by means of concentrated aqueous HCl. The precipitate which formed was filtered off with suction, dried and heated at 130° C. for 1 hour, giving 236 g (93%) of 13 as a viscous oil.

Fuente