Diethyl Malonate → Diethyl (ethoxymethylene)malonate

HRID 2248978Notes

Reaction equation

HRID 2248978 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH:12](OCC)(OCC)[O:13][CH2:14][CH3:15].C(OC(=O)C)(=O)C>OP(O)(O)=O>[CH2:14]([O:13][CH:12]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])[CH3:15]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformate2×

Product 1

HCID 6871Diethyl (ethoxymethylene)malonateYield 92.6%

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidCatalyst

Procedure

160.2 g (1.0 mol) of diethyl malonate, 474.2 g (3.2 mol) of triethyl orthoformate and 0.5 g of catalyst from Example 5 were initially introduced and the mixture was heated to boiling. A mixture of 10 g of acetic anhydride, 1 g of H3PO4 and 30 g of triethyl orthoformate were continuously added dropwise over the course of 6 hours. The reaction and work up were carried out in accordance with Example 3 and gave 200 g of diethyl ethoxymethylenemalonate, which corresponds to a yield of 92.6% of the theoretical yield.

Workup

  1. temperaturethe mixture was heated to boiling
  2. additionwere continuously added dropwise over the course of 6 hours
  3. customThe reaction and work

Sources & evidence

ORD record
ord-69f78ba747424b56bfff154c96b11279
Source dataset
uspto-grants-1991_08
Patent number
US05041619

Reaction notes

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