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

HRID 1526895Notes

Reaction equation

HRID 1526895 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][CH:7]([C:12]([O:14]C)=[O:13])[C:8]([O:10]C)=[O:9])=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]([C:8]([OH:10])=[O:9])[C:12]([OH:14])=[O:13])=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 2801290Dimethyl 2-(4-bromobenzyl)malonate

Product 1

HCID 133302152-(4-Bromobenzyl)malonic acidYield 91%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of dimethyl 2-(4-bromobenzyl)malonate (22 g, 73.33 mmol, 1.00 equiv) and potassium hydroxide (12.3 g, 219.64 mmol, 3.00 equiv) in ethanol (140 mL) and water (140 mL) was stirred at 60° C. overnight. The resulting solution was diluted with 300 mL of ice and water then extracted with 1×500 mL of ethyl acetate. The organic layer was washed with 2×150 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 18.2 g (91%) of 2-(4-bromobenzyl)malonic acid as a white solid.

Workup

  1. extractionthen extracted with 1×500 mL of ethyl acetate
  2. washThe organic layer was washed with 2×150 mL of brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f1a12c078c724ca28aa04eeb3cd7f632
Source dataset
uspto-grants-2015_07
Patent number
US09085570B2

Reaction notes

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