Hydrochloric Acid → Monoethyl malonate

HRID 2074214Notes

Reaction equation

HRID 2074214 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][C:3]([OH:5])=[O:4].[CH2:8]([K])[CH3:9].Cl>O>[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178461627HCID 178461627, compound

Product 1

HCID 70615Monoethyl malonateYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl potassium malonate (25.0 g, 0.15 mol) was suspended in water (15.6 ml) and cooled in an ice bath. Concentrated HCl (12.5 ml) was added dropwise over 30 min, then the mixture was stirred for a further 10 min. The precipitate was filtered, then washed twice with ether. The filtrate was separated and the aqueous phase was extracted with ether. The combined ethereal solutions were dried (MgSO4) and evaporated to afford, as an oil, monoethyl hydrogen malonate (19.2 g, 99%) which was dried under vacuum overnight (or 50°/1 mm for 1 h) prior to use.

Workup

  1. temperaturecooled in an ice bath
  2. filtrationThe precipitate was filtered
  3. washwashed twice with ether
  4. customThe filtrate was separated
  5. extractionthe aqueous phase was extracted with ether
  6. dry with materialThe combined ethereal solutions were dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-0118ab4e7915412cbbf24f082bacbbae
Source dataset
uspto-grants-2011_04
Patent number
US07919497B2

Reaction notes

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