Acetic Acid → Diethyl 2-butenedioate

HRID 1082747Notes

Reaction equation

HRID 1082747 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3](OCC)=O.C=O.[C:14]([O-:17])(=[O:16])C.[K+].[C:19](O)(=O)[CH3:20]>O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH2:19]([O:17][C:14]([CH:3]=[CH:2][C:1]([O:9][CH2:10][CH3:11])=[O:8])=[O:16])[CH3:20]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 7761Diethyl MalonateHCID 517044Potassium Acetate

Product 1

HCID 12201Diethyl 2-butenedioate

Reagents, catalysts & solvents 1

HCID 165397Cupric acetate monohydrateCatalyst

Procedure

A mixture of 80 g of diethyl malonate, 30 g of paraformaldehyde, 5 g of potassium acetate, 5 g of copper (II) acetate monohydrate and 200 ml of acetic acid was heated at 90° to 100° C. for 2 hours. Acetic acid was removed from the reaction mixture under reduced pressure, and the residue was evaporated under reduced pressure to obtain 44 g of bis(ethoxycarbonyl)ethylene.

Workup

  1. temperaturewas heated at 90° to 100° C. for 2 hours
  2. customAcetic acid was removed from the reaction mixture under reduced pressure
  3. customthe residue was evaporated under reduced pressure

Sources & evidence

ORD record
ord-eb374d9be42c45a495138a419492018f
Source dataset
uspto-grants-1996_12
Patent number
US05589592

Reaction notes

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