Water → HCID 88790504, compound

HRID 1447912Notes

Reaction equation

HRID 1447912 reaction equation
[C:1]([O:9]CC)(=O)[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].Cl[CH2:13][CH:14]=[CH:15]CCl.O.[CH3:19][CH2:20]OCC>C(O)C>[CH2:6]([O:5][C:3]1([O:4][CH2:19][CH3:20])[C:2](=[C:1]=[O:9])[CH:13]1[CH:14]=[CH2:15])[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 7761Diethyl MalonateHCID 151221,4-Dichloro-2-butene

Product 1

HCID 88790504HCID 88790504, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 18.4 g (2 equivalents) in 300 ml of anhydrous ethanol is added rapidly 164 g (1 equivalent) of diethyl malonate. 1,4-Dichloro-2-butene (98% mixture of cis and trans, Aldrich) (50 g, 1 equivalent) is slowly added to the warm, stirred suspension of the diethyl sodio malonate during 15 minutes after which the mixture is refluxed for 3 hours. Upon cooling, the mixture is poured into 1.2 liters of water and an oil isolated by ether extraction. The ether extract is dried over magnesium sulfate and distilled to give 1,1-bis-ethoxy-carbonyl-2-vinylcyclopropane, B.P. 108°-116° C./14 mm.

Workup

  1. temperatureis refluxed for 3 hours
  2. temperatureUpon cooling
  3. extractionThe ether extract
  4. dry with materialis dried over magnesium sulfate
  5. distillationdistilled

Sources & evidence

ORD record
ord-e3aefee35d9c439eb1fb6c26e366bba8
Source dataset
uspto-grants-1979_12
Patent number
US04178463

Reaction notes

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