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

HRID 1004784
Notes
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Reaction equation

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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8610Diethyl ethylmalonateHCID 14797Potassium HydroxideHCID 2633651-(Bromomethyl)-2-phenylbenzeneHCID 5360545Sodium

Product 1

HCID 215719833-(2-Biphenylyl)-2-ethylpropionic acidYield 93%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent
4×

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

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

Sources & evidence

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

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes