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

HRID 747077Notes

Reaction equation

HRID 747077 reaction equation
[CH3:1][C:2](=[N:4][OH:5])[CH3:3].Cl[CH2:7][C:8]([OH:10])=[O:9].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:1][C:2](=[N:4][O:5][CH2:7][C:8]([OH:10])=[O:9])[CH3:3]

Participants

6

Reactant 3

HCID 300Chloroacetic AcidHCID 14798Sodium HydroxideHCID 67180Acetone, oxime

Product 1

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

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

7.3 g of acetone oxime, 14.2 g of chloroacetic acid and 2% of tetrabutylammonium bromide are placed in 80 ml of toluene. An aqueous sodium hydroxide solution (10 g of sodium hydroxide dissolved in 150 ml of water) is added dropwise. The reaction medium is stirred for 1 h and then the toluene is evaporated under vacuum. The residue is then acidified with concentrated hydrochloric acid to pH 2.5, then washed with water and extracted twice with ethyl acetate. The organic phase is dried over sodium sulfate and the solvent is evaporated to give the expected product.

Workup

  1. customthe toluene is evaporated under vacuum
  2. washwashed with water
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customthe solvent is evaporated

Sources & evidence

ORD record
ord-20988d9a1e434193b54ddb81c32a440b
Source dataset
uspto-grants-2008_07
Patent number
US07396525B2

Reaction notes

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