Sodium Bicarbonate → 3-t-Butylperoxy-1,3-dimethylbutyl Hydrogen Oxalate

HRID 361954Notes

Reaction equation

HRID 361954 reaction equation
[C:1](Cl)(=[O:17])[C:2]([O:4][CH:5]([CH3:16])[CH2:6][C:7]([O:10][O:11][C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:9])[CH3:8])=[O:3].C([O-])(O)=[O:20].[Na+]>O>[C:2]([O:4][CH:5]([CH3:16])[CH2:6][C:7]([O:10][O:11][C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:9])[CH3:8])(=[O:3])[C:1]([OH:17])=[O:20]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 19612334HCID 19612334, compound

Product 1

HCID 571962123-t-Butylperoxy-1,3-dimethylbutyl Hydrogen Oxalate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 50 mL Erlenmeyer flask equipped with a magnetic stirrer and a thermometerwas charged with 50 g of water and 2.8 g (10 mmoles) of 3-t-butylperoxy-1,3-dimethylbutyl chlorooxalate and the resulting mixture was stirred at room temperature. No reaction appeared to be occurring, therefore, 2.1 g (23 mmoles) of NaHCO3 was added. Gas evolution occurred and the organic liquid dissolved in the aqueous phase at room temperature. The pH of the solution was about 9. The aqueous solution was washed twice with 30 mL portions of MTBE in order to remove neutral impurities. Then the aqueous solution was acidified with 20 g (27 mmoles) of aqueous 5% HCl solution and a yellow organic liquid formed. The resulting mixture was extracted twice with 30 mL portions of MTBE. The MTBE extracts were combined, washed once with 50 mL of water, dried over 5% by weight of anhydrous MgSO4, and, after separation of the spent desiccant by filtration, the solvent was removed in vacuo leaving 2.2 g (85% of theory, uncorrected) of a clear yellow liquid. An IR spectrum of the product showed an acid OH band at about 3200 cm-1, a very strong carbonyl band at 1740 cm-1 and a peroxide (--OO--) band at about 875 cm-1.

Workup

  1. customA 50 mL Erlenmeyer flask equipped with a magnetic stirrer
  2. dissolutionthe organic liquid dissolved in the aqueous phase at room temperature
  3. washThe aqueous solution was washed twice with 30 mL portions of MTBE in order
  4. customto remove neutral impurities
  5. customa yellow organic liquid formed
  6. extractionThe resulting mixture was extracted twice with 30 mL portions of MTBE
  7. washwashed once with 50 mL of water
  8. dry with materialdried over 5% by weight of anhydrous MgSO4
  9. customafter separation of the spent desiccant
  10. filtrationby filtration
  11. customthe solvent was removed in vacuo
  12. customleaving 2.2 g (85% of theory, uncorrected) of a clear yellow liquid

Sources & evidence

ORD record
ord-a8203ccde53044368b9a71563e9e941b
Source dataset
uspto-grants-1999_02
Patent number
US05866712

Reaction notes

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