Potassium Hydroxide → 2-Butynedioic acid, potassium salt (1:2)

HRID 638347Notes

Reaction equation

HRID 638347 reaction equation
[OH-].[K+:2].Br[CH:4]([CH:8](Br)[C:9]([OH:11])=[O:10])[C:5]([OH:7])=[O:6]>CO>[K+:2].[K+:2].[C:8]([C:9]([O-:11])=[O:10])#[C:4][C:5]([O-:7])=[O:6]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 953242,3-Dibromosuccinic acid

Product 1

HCID 99423542-Butynedioic acid, potassium salt (1:2)Yield 233.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of potassium hydroxide (44.8 g) and methanol (200 ml) was added 2,3-dibromosuccinic acid (55.2 g), and the whole was heated under reflux for 5 hours over a water bath. After cooling, white crystals were filtered and washed with methanol to afford a mixture (89 g) of acetylenedicarboxylic acid di-potassium salt and potassium bromide. The mixture was dissolved in water (as little water as possible was used) and 6N sulfuric acid (36 ml) was carefully added. White crystals formed were filtered to give 12.8 g of acetylenedicarboxylic acid mono-potassium salt.

Workup

  1. temperaturethe whole was heated
  2. temperatureunder reflux for 5 hours over a water bath
  3. temperatureAfter cooling
  4. filtrationwhite crystals were filtered
  5. washwashed with methanol

Sources & evidence

ORD record
ord-b38ec3e262dd4e189e78e830d4c3a74c
Source dataset
uspto-grants-1985_12
Patent number
US04560763

Reaction notes

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