Acetyl chloride → 2,3-Diacetoxypropanoic acid

HRID 1645487Notes

Reaction equation

HRID 1645487 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[OH:5][CH:6]([CH2:10][OH:11])[C:7]([O-:9])=[O:8].[Li+].[C:13](OCC)(=[O:15])[CH3:14]>>[C:1]([O:5][CH:6]([CH2:10][O:11][C:13](=[O:15])[CH3:14])[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 8857Ethyl AcetateHCID 59824357Lithium 2,3-dihydroxypropanoate

Product 1

HCID 147372062,3-Diacetoxypropanoic acid

Procedure

Acetyl chloride (500 ml) was added dropwise without stirring to the gummy like mass of lithium 2,3-dihyroxypropanoate (13) (171 g, 1.51 mole). The gummy like mass dissolved slowly and the mixture was left for 24 h at ambient temperature. Then the mixture was stirred and heated to reflux for 6 h. After cooling the mixture was diluted with ethyl acetate (700 ml) and filtered through a tight glass filter (por. G4). The filtrate was evaporated to a oil, which was dissolved in ethyl acetate (750 ml) and washed with water (2×70 ml, pH=2). After drying over magnesium sulfate and treatment with activated charcoal (1.5 g) the mixture was filtered. The filtrate was evaporated to a light orange coloured oil. Yield (crude) 218 g (75%).

Workup

  1. dissolutionThe gummy like mass dissolved slowly
  2. temperatureheated
  3. temperatureto reflux for 6 h
  4. temperatureAfter cooling the mixture
  5. filtrationfiltered through a tight glass
  6. filtrationfilter (por. G4)
  7. customThe filtrate was evaporated to a oil, which
  8. dissolutionwas dissolved in ethyl acetate (750 ml)
  9. washwashed with water (2×70 ml, pH=2)
  10. dry with materialAfter drying over magnesium sulfate and treatment with activated charcoal (1.5 g) the mixture
  11. filtrationwas filtered
  12. customThe filtrate was evaporated to a light orange coloured oil
  13. customYield (crude) 218 g (75%)

Sources & evidence

ORD record
ord-259c225afa9c4b28aa34feedad912be9
Source dataset
uspto-grants-2012_02
Patent number
US08124806B2

Reaction notes

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