Sulfuric Acid → Methyl (1,1-dimethyl-2-oxopropoxy)acetate

HRID 478293Notes

Reaction equation

HRID 478293 reaction equation
[CH3:1][O:2][C:3](=[O:11])[CH2:4][O:5][C:6]([CH3:10])([CH3:9])[C:7]#[CH:8].S(=O)(=O)(O)[OH:13]>CO.C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[CH3:10][C:6]([CH3:9])([O:5][CH2:4][C:3]([O:2][CH3:1])=[O:11])[C:7](=[O:13])[CH3:8]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 13005744(1,1-Dimethylprop-2-ynyloxy)acetic acid methyl ester

Product 1

HCID 85791200Methyl (1,1-dimethyl-2-oxopropoxy)acetate

Reagents, catalysts & solvents 2

HCID 15337Mercuric acetateCatalystHCID 887MethanolSolvent

Procedure

The product from Example 66A (10.0 g, 64 mmol) in methanol (320 mL) was treated with mercury(II) acetate (2.0 g, 6.4 mmol) and sulfuric acid (0.5 mL). After refluxing for 1.5 hours, the mixture was allowed to cool to ambient temperature, concentrated to a volume of 100 mL, poured into 1N HCl (300 mL) and extracted with dichloromethane (3×300 mL). The organic layers were combined, washed with aqueous NaHCO3, washed with brine, dried over Na2SO4 and concentrated to provide the title compound (10.3 g).

Workup

  1. temperatureAfter refluxing for 1.5 hours
  2. concentrationconcentrated to a volume of 100 mL
  3. additionpoured into 1N HCl (300 mL)
  4. extractionextracted with dichloromethane (3×300 mL)
  5. washwashed with aqueous NaHCO3
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-de07702b94b549d98520e0305c476907
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Reaction notes

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