Methanol → Methyl (1-methyl-2-oxopropoxy)acetate

HRID 478303Notes

Reaction equation

HRID 478303 reaction equation
[CH3:1][CH:2]([O:5][CH2:6][C:7]([O:9][CH3:10])=[O:8])[C:3]#[CH:4].C[OH:12]>C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[CH3:1][CH:2]([O:5][CH2:6][C:7]([O:9][CH3:10])=[O:8])[C:3](=[O:12])[CH3:4]

Participants

4

Reactant 2

HCID 887MethanolHCID 18619750Methyl [(1-methyl-2-propynyl)oxy]acetate

Product 1

HCID 71360827Methyl (1-methyl-2-oxopropoxy)acetate

Reagents, catalysts & solvents 1

HCID 15337Mercuric acetateCatalyst

Procedure

The product from Example 84A (20 g, 0.14 mol) in methanol (700 mL) was treated with mercury(II) acetate (4.6 g, 0.014 mol), heated to reflux for 1 hour, concentrated to approximately 100 mL total volume, treated with 1M HCl (100 mL) and extracted with dichloromethane (3×, 100 mL). The extractions were combined, dried (MgSO4), filtered and concentrated to provide the title compound.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. concentrationconcentrated to approximately 100 mL total volume
  4. additiontreated with 1M HCl (100 mL)
  5. extractionextracted with dichloromethane (3×, 100 mL)
  6. extractionThe extractions
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9f1dc2b8afbf41bd9233f749e5179f92
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Reaction notes

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