Diethyl ethylmalonate → 3-(2-Biphenylyl)-2-ethylpropionic acid

HRID 964775

Reaktionsgleichung

[CH2:1]([CH:3]([C:9](OCC)=O)[C:4]([O:6]CC)=[O:5])[CH3:2].[Na].[C:15]1([C:21]2[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=2CBr)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[K+]>O>[C:15]1([C:21]2[CH:22]=[CH:25][CH:26]=[CH:27][C:28]=2[CH2:9][CH:3]([CH2:1][CH3:2])[C:4]([OH:6])=[O:5])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

Reaktionsbedingungen

Temperatur: 130 °C

Versuchsvorschrift

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.

Aufarbeitung

temperaturethe mixture was refluxed for 3 hours
additionwere added at room temperature
temperaturethe mixture was refluxed for a further 4 hours
customThe solvent was removed in vacuo, H2O
additionwas added to the residue until the latter
dissolutionhad dissolved completely
customThe precipitate which formed
filtrationwas filtered off with suction
customdried

Quellen und Nachweise

ORD-Eintrag: ord-72390fd5113f4af1b49b561ff371da45
Quelldatensatz: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05770753

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