Diethyl Malonate → HCID 18784169, compound

HRID 1108753Notes

Reaction equation

HRID 1108753 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5]CC)=O.CC(C)([O-])C.[K+].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:28]=[CH:29][C:30](=[O:32])[CH3:31])[CH:23]=[CH:24][C:25]=1[O:26][CH3:27]>C(O)C>[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:28]2[CH2:29][C:30](=[O:32])[CH2:31][C:3](=[O:5])[CH:2]2[C:1]([O:9][CH2:10][CH3:11])=[O:8])[CH:23]=[CH:24][C:25]=1[O:26][CH3:27]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 847484-(3,4-Dimethoxyphenyl)but-3-en-2-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 18784169HCID 18784169, compoundYield 871.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Diethyl malonate (73. 7 g) was dissolved in ethanol (700 ml), and then potassium tert-butoxide (51.6 g) was gradually added thereto. A solution of 4-(3,4-dimethoxyphenyl)-3-buten-2-one (79.1 g) in ethanol (500 ml) was added dropwise, and the mixture was refluxed for 1.5 hours. After distilling off the reaction solvent under reduced pressure, ice water was poured over it and it was adjusted to pH4 with concentrated hydrochloric acid. The deposited crystals were filtered by suction, washed with water and then air-dried to give 122 g of ethyl 2-(3,4-dimethoxyphenyl)-4,6-dioxocyclohexane carboxylate (99.6%).

Workup

  1. temperaturethe mixture was refluxed for 1.5 hours
  2. distillationAfter distilling off the reaction solvent under reduced pressure, ice water
  3. additionwas poured over it and it
  4. filtrationThe deposited crystals were filtered by suction
  5. washwashed with water
  6. customair-dried

Sources & evidence

ORD record
ord-9c21202cffce45829b9f67d9e3bde488
Source dataset
uspto-grants-2000_05
Patent number
US06069176

Reaction notes

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