Potassium Hydroxide → 2-(4-Bromobenzyl)malonic acid

HRID 472951Notes

Reaction equation

HRID 472951 reaction equation
[Br:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][CH:7]([C:13]([O:15]CC)=[O:14])[C:8]([O:10]CC)=[O:9])=[CH:4][CH:3]=1.[OH-].[K+]>OC(C)=O.O.C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]([C:8]([OH:10])=[O:9])[C:13]([OH:15])=[O:14])=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 10860456Diethyl 2-(4-bromobenzyl)malonate

Product 1

HCID 133302152-(4-Bromobenzyl)malonic acidYield 873.2%

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

Diethyl 2-(4-bromobenzyl)malonate (40 g, 13 mmol) and KOH (42.8 g, 76 mmol) was dissolved in a mixture of HOAc-H2O-THF (1:2:3, 200 mL), the mixture was refluxed for 12 hours. The solvent was removed in vacuo, the residue was added HCl aqueous, then extracted with EtOAc, washed with brine, dried over Na2SO4, concentrated to give 2-(4-bromobenzyl)malonic acid (31 g, 95%).

Workup

  1. temperaturethe mixture was refluxed for 12 hours
  2. customThe solvent was removed in vacuo
  3. additionthe residue was added HCl aqueous
  4. extractionextracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-01c7f3098df2413bb1bdfff583d7c8cd
Source dataset
uspto-grants-2014_01
Patent number
US08633212B2

Reaction notes

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