Bromoacetic Acid → [(2-Propanylideneamino)oxy]acetic acid

HRID 386119Notes

Reaction equation

HRID 386119 reaction equation
Br[CH2:2][C:3]([OH:5])=[O:4].[OH-].[Na+].[CH3:8][C:9](=[N:11][OH:12])[CH3:10]>>[CH3:8][C:9](=[N:11][O:12][CH2:2][C:3]([OH:5])=[O:4])[CH3:10]

Participants

4

Reactant 3

HCID 6227Bromoacetic AcidHCID 14798Sodium Hydroxide2×HCID 67180Acetone, oxime

Product 1

HCID 79344[(2-Propanylideneamino)oxy]acetic acid

Procedure

To bromoacetic acid (500 g, 3.60 mol) and ice (400 g) was added dropwise 40% sodium hydroxide (375 g, 3.75 mol) at below 20° C. Acetone oxime (239 g, 3.27 mol) was added. At below 20° C., 40% sodium hydroxide (375 g, 3.27 mol) was added dropwise. The reaction mixture was allowed to warm to room temperature overnight and extracted with 500 ml of ether. The aqueous phase was acidified to pH 2 and extracted with ether (3×500 ml). The combined organic layers were dried over MgSO4, filtered, and concentrated to dryness. Hexane (250 ml) was added to the residue and the precipitate was collected to give the title compound.

Workup

  1. extractionextracted with 500 ml of ether
  2. extractionextracted with ether (3×500 ml)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. additionHexane (250 ml) was added to the residue
  7. customthe precipitate was collected

Sources & evidence

ORD record
ord-860c3ea72f5e459b81356b064cc1d325
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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