HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Itaconic acid → Sodium 5-oxo-2,5-dihydrofuran-3-carboxylate

HRID 83521
Notes
Print preview

Reaction equation

HRID 83521 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]([CH2:4][C:5]([OH:7])=[O:6])=[CH2:3].BrBr.C(=O)([O-])O.[Na+:16].C(=O)([O-])[O-].[Na+].[Na+]>O>[O:6]=[C:5]1[O:7][CH2:3][C:2]([C:1]([O-:9])=[O:8])=[CH:4]1.[Na+:16]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 811Itaconic acidHCID 10340Sodium CarbonateHCID 24408BromineHCID 516892Sodium Bicarbonate

Product 1

HCID 86680361Sodium 5-oxo-2,5-dihydrofuran-3-carboxylateYield 56%

Reagents, catalysts & solvents 1

HCID 962Water
Solvent
2×

Conditions

Temperature
30 °C

Procedure

To a solution of itaconic acid (26.0 g) in water (35 ml) was added dropwise bromine (10.3 ml) at room temperature while keeping a temperature of the reaction solution below 45° C., and then the mixture was stirred at 30° C. for 15 minutes. To this reaction solution was added portionwise sodium hydrogen carbonate (33.6 g), and then the mixture was heated to 55° C. To this reaction solution was added dropwise a solution of sodium carbonate (10.6 g) in water (15 ml), and then the mixture was stirred for 20 minutes. This reaction solution was iced, and stirred for 1 hour. The precipitated solid was collected by filtration, washed with cold water and ethanol, and then dried under reduced pressure to give the titled compound (16.8 g).

Workup

  1. customa temperature of the reaction solution below 45° C.
  2. temperaturethe mixture was heated to 55° C
  3. stirringthe mixture was stirred for 20 minutes
  4. stirringstirred for 1 hour
  5. filtrationThe precipitated solid was collected by filtration
  6. washwashed with cold water and ethanol
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-229ae9931b90416da53922cb27a1b3f5
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846746B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes