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Sulfuric Acid → 2-(1,1-Dimethyl-2-oxopropoxy)propionic acid methyl ester

HRID 341649
Notes
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Reaction equation

HRID 341649 reaction equation
S(=O)(=O)(O)[OH:2].[CH3:6][O:7][C:8](=[O:17])[CH:9]([O:11][C:12]([CH3:16])([CH3:15])[C:13]#[CH:14])[CH3:10]>C([O-])(=O)C.[Hg+2].C([O-])(=O)C.O>[CH3:6][O:7][C:8](=[O:17])[CH:9]([O:11][C:12]([CH3:16])([CH3:15])[C:13](=[O:2])[CH3:14])[CH3:10]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 595626712-(1,1-Dimethylprop-2-ynyloxy)propionic acid methyl ester

Product 1

HCID 595625612-(1,1-Dimethyl-2-oxopropoxy)propionic acid methyl esterYield 141.7%

Reagents, catalysts & solvents 2

HCID 15337Mercuric acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of mercury (II) acetate (7.76 g, 0.024 mol), sulfuric acid (9 ml, 0.09 mol) and water (450 ml) is heated at 60° C. 2-(1,1-dimethylprop-2-ynyloxy)propionic acid methyl ester (90 g, 0.529 mol) is added carefully at 60° C. The reaction mixture is maintained at 60° C. for 8 hours and cooled to ambient temperature. The aqueous phase is extracted with diethyl ether (3×250 ml), the organic phases are combined, washed with water, and dried over anhydrous sodium sulfate. The mixture is filtered, and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give 2-(1,1-dimethyl-2-oxopropoxy)propionic acid methyl ester (24 g) as a colorless oil.

Workup

  1. temperatureThe reaction mixture is maintained at 60° C. for 8 hours
  2. temperaturecooled to ambient temperature
  3. extractionThe aqueous phase is extracted with diethyl ether (3×250 ml)
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe mixture is filtered
  7. customthe filtrate is evaporated under reduced pressure
  8. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d4ab15b6213542d2ab6ddd1709c55b24
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08895761B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes