Diethyl methylmalonate → 3-Methoxy-2-methyl-3-oxopropanoic acid

HRID 1665674

Reaction equation

HRID 1665674 reaction equation
[OH-].[K+].[CH2:3]([O:5][C:6](=[O:14])[CH:7]([CH3:13])[C:8]([O:10]CC)=[O:9])C>CO>[CH3:3][O:5][C:6](=[O:14])[CH:7]([CH3:13])[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 11857Diethyl methylmalonateHCID 14797Potassium Hydroxide

Product 1

HCID 3006933-Methoxy-2-methyl-3-oxopropanoic acidYield 47.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

KOH (386 mg, 6.88 mmol) was added to a solution 2-methyl-malonic acid diethyl ester (1 g, 5.74 mmol) in methanol (7 mL). The resulting mixture was stirred overnight at ambient temperature then concentrated. The resulting residue was diluted with water, acidified with conc. HCl and the product was extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford 360 mg (47%) of 2-methyl-malonic acid monomethyl ester

Workup

  1. concentrationthen concentrated
  2. additionThe resulting residue was diluted with water
  3. extractionthe product was extracted with dichloromethane
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ffa459bab6874c01a1a05d203d9280f9
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Linked notes

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