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

HRID 341649Notes

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]

Participants

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

temperatureThe reaction mixture is maintained at 60° C. for 8 hours
temperaturecooled to ambient temperature
extractionThe aqueous phase is extracted with diethyl ether (3×250 ml)
washwashed with water
dry with materialdried over anhydrous sodium sulfate
filtrationThe mixture is filtered
customthe filtrate is evaporated under reduced pressure
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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