Sulfuric Acid → methyl (2-oxopropoxy)acetate

HRID 987376Notes

Reaction equation

HRID 987376 reaction equation
[CH2:1]([O:4][CH2:5][C:6]([O:8][CH3:9])=[O:7])[C:2]#[CH:3].S(=O)(=O)(O)[OH:11]>CO.C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[O:11]=[C:2]([CH3:3])[CH2:1][O:4][CH2:5][C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 10877131Methyl 2-(prop-2-yn-1-yloxy)acetate

Product 1

HCID 11701055methyl (2-oxopropoxy)acetate

Reagents, catalysts & solvents 2

HCID 15337Mercuric acetateCatalystHCID 887MethanolSolvent

Procedure

The product from Example 1A (56 g, 0.44 mol) in methanol (1.5 L) was treated with mercury(II) acetate (14 g, 44 mmol), treated with concentrated sulfuric acid (3 mL), refluxed for 1 hour, allowed to cool to ambient temperature, concentrated to a volume of 200 mL, treated with 1M HCl (500 mL) and extracted with dichloromethane (thrice, 300 mL). The combined dichloromethane layers were dried (MgSO4), filtered, concentrated and distilled (65-95° C. at 1 torr) to provide the title compound.

Workup

  1. temperaturerefluxed for 1 hour
  2. concentrationconcentrated to a volume of 200 mL
  3. additiontreated with 1M HCl (500 mL)
  4. extractionextracted with dichloromethane (thrice, 300 mL)
  5. dry with materialThe combined dichloromethane layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. distillationdistilled (65-95° C. at 1 torr)

Sources & evidence

ORD record
ord-2465d680036b4727a5e734aee66f20ce
Source dataset
uspto-grants-2003_10
Patent number
US06632418B2

Reaction notes

Loading…