Dimethyl malonate → HCID 14578420, compound

HRID 981867Notes

Reaction equation

HRID 981867 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11](=[O:13])[CH3:12])=[CH:5][CH:4]=1)[CH3:2].C(OC)(=O)[CH2:15][C:16](OC)=[O:17].C[O-].[Na+]>CO>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:10][C:11](=[O:13])[CH:12]=[C:16]([OH:17])[CH2:15]2)=[CH:5][CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 10942334Sodium MethoxideHCID 53892677HCID 53892677, compound

Product 1

HCID 14578420HCID 14578420, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

144 g (0.83 mol) of 4-(4-ethylphenyl)-3-buten-2-one dissolved in a small amount of methanol is dripped into 109 g (0.83 mol) of dimethyl malonate and 45 g (0.83 mol) of sodium methylate in 40 ml of methanol. The mixture is stirred at reflux for 3 hours and for 10 hours at room temperature. The methanol is distilled off, and the residue is taken up in 2 liters of 10% strength potassium hydroxide solution and stirred for 8 hours at room temperature. At 60° C., the mixture is acidified to pH 1 with concentrated hydrochloric acid. The mixture is stirred for a further 2 hours and suction filtered, and the precipitate is dried under reduced pressure.

Workup

  1. distillationThe methanol is distilled off
  2. stirringstirred for 8 hours at room temperature
  3. customAt 60° C.
  4. stirringThe mixture is stirred for a further 2 hours
  5. filtrationsuction filtered
  6. customthe precipitate is dried under reduced pressure

Sources & evidence

ORD record
ord-5692aafd09ed441c940fc01cbccf116b
Source dataset
uspto-grants-1991_02
Patent number
US04994106

Reaction notes

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