Oxalic Acid → diallyloxyacetic acid

HRID 2379243Notes

Reaction equation

HRID 2379243 reaction equation
C(OCC)C.C(O)(=O)C(O)=O.[CH2:12]([O:15][CH:16]([O:20][CH2:21][CH:22]=[CH2:23])[C:17]([O-:19])=[O:18])[CH:13]=[CH2:14].[Na+]>O>[CH2:21]([O:20][CH:16]([O:15][CH2:12][CH:13]=[CH2:14])[C:17]([OH:19])=[O:18])[CH:22]=[CH2:23]

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 3283Diethyl EtherHCID 5173263Sodium diallyloxyacetate

Product 1

HCID 5173264diallyloxyacetic acidYield 93.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

100 g of diethyl oxide then a solution of 17.6 g (0.14 mole) of oxalic acid crystallised with two molecules of water in 62 g of water are introduced at ambient temperature and under agitation into an aqueous solution containing 29.1 g (0.15hole) of sodium diallyloxyacetate in 71 g of water. The biphasic medium obtained is agitated vigorously for 10 minutes then it is decanted. The ethereal phase is then dried over anhydrous sodium sulphate, filtered and finally concentrated to dryness under vacuum. In this way 24 g (0.14 mole) of pure diallyloxyacetic acid is obtained. This acid is in the form of an oil, it has a pka of 2.9 and it is soluble in water and in standard organic solvents such as diethyl oxide, dichloromethane; however, in aqueous solution, it hydrolyses.

Workup

  1. additionare introduced at ambient temperature and under agitation into an aqueous solution
  2. customThe biphasic medium obtained
  3. customit is decanted
  4. dry with materialThe ethereal phase is then dried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationfinally concentrated to dryness under vacuum

Sources & evidence

ORD record
ord-8b49cea40c4a4be99ecfe84cc7c449ac
Source dataset
uspto-grants-1994_11
Patent number
US05360881

Reaction notes

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