Ethanol → 3-(2-phenylphenyl)propionic acid

HRID 356829Notes

Reaction equation

[C:1]1([C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[CH2:9]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:15].[K+].[CH3:17][CH2:18][OH:19]>O.C(OCC)(=O)CC(OCC)=O.[Na]>[C:1]1([C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[CH2:9][CH2:17][C:18]([OH:15])=[O:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 130 °C

Procedure

93 cm3 (0.61 mmol) of diethyl malonate dissolved in 50 cm3 of H2P-free EtOH were added dropwise at room temperature to 14 g (0.61 mmol) of sodium in 400 cm3 of H2O-free EtOR. 150 g (0.61 mmol) of 2-phenylbenzyl bromide in 200 cm3 of H2O-free EtOH were subsequently added dropwise, and the mixture was refluxed for 3 hours. 102 g (1.83 mol) of KOH dissolved in 150 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 dissolved completely, and the mixture was 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 112 g (81%) of 8 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
dissolutionlatter dissolved completely
customThe precipitate which formed
filtrationwas filtered off with suction
customdried

Sources & evidence

ORD record: ord-74d23a3ba2614b5eb5f6eb3656651198
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840644

Reaction notes

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