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

HRID 1004784

Reaction equation

[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

Participants

Conditions

Temperature: 130 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-524b6156d7d0407088a9f76a0254d3e6
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06051727

Linked notes

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