Hydrochloric Acid → Monoethyl malonate

HRID 887973Notes

Reaction equation

HRID 887973 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-f520997e7f234f07aa6519028126fc74
Source dataset
uspto-grants-2012_08
Patent number
US08247552B2

Reaction notes

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