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

HRID 1862443Notes

Reaction equation

HRID 1862443 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

A solution of the product from Example 43A (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 heating the reaction mixture at reflux for 1.5 hours, the mixture was allowed to cool to ambient temperature and then concentrated to a volume of 100 mL. The reaction mixture was poured into 1N HCl (300 mL) and extracted with dichloromethane (3×300 mL). The organic layers were combined, washed with NaHCO3, washed with brine, dried over Na2SO4, and concentrated to provide the title compound (10.3 g). 1H NMR (CDCl3) δ 1.34 (s, 6H), 2.25 (s, 3H), 3.76 (s, 3H), 4.01 (s, 2H).

Workup

  1. temperatureAfter heating the reaction mixture
  2. temperatureat reflux for 1.5 hours
  3. concentrationconcentrated to a volume of 100 mL
  4. additionThe reaction mixture was poured into 1N HCl (300 mL)
  5. extractionextracted with dichloromethane (3×300 mL)
  6. washwashed with NaHCO3
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b70641aee730443b9680104a0221d4ba
Source dataset
uspto-grants-2003_03
Patent number
US06538004B2

Reaction notes

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