Hydrochloric Acid → HCID 19907376, compound

HRID 2371522Notes

Reaction equation

HRID 2371522 reaction equation
[Na].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].Br[CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25]Br)=[CH:19][CH:18]=1.Cl>C(O)C>[CH2:11]([O:10][C:2]([CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]([O:10][CH2:11][CH3:12])=[O:9])=[CH:19][CH:18]=1)=[O:9])[CH3:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl Malonate2×HCID 5360545SodiumHCID 135926591,4-Bis(3-bromopropyl)benzene

Product 1

HCID 19907376HCID 19907376, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

First, to 483 mg of metallic sodium dissolved in 21 ml of absolute ethanol, 6.72 g of diethyl malonate was added dropwise, and the mixture was refluxed for 5 minutes. After cooling, to the solution was added dropwise a mixture of 3.2 g of 1,4-bis(3-bromopropyl)benzene and diethyl malonate over 5 minutes, and the mixture was refluxed for 40 minutes to obtain a white suspension. After cooling and addition of 21 ml of ice water, the mixture was adjusted to pH 7.0 with 1N hydrochloric acid, and ethanol was removed under a reduced pressure to obtain an aqueous layer, which was then twice extracted with 100 ml of benzene each time. The extract was washed with a saturated sodium chloride aqueous solution, dried over magnesium sulfate and evaporated under a reduced pressure to remove the solvent, and then to remove any unreacted diethyl malonate under a reduced pressure at 140° C. to obtain 4.74 g of the title compound as a colorless liquid.

Workup

  1. temperaturethe mixture was refluxed for 5 minutes
  2. temperatureAfter cooling, to the solution
  3. additionwas added dropwise
  4. temperaturethe mixture was refluxed for 40 minutes
  5. customto obtain a white suspension
  6. temperatureAfter cooling
  7. customwas removed under a reduced pressure
  8. customto obtain an aqueous layer, which
  9. extractionwas then twice extracted with 100 ml of benzene each time
  10. washThe extract was washed with a saturated sodium chloride aqueous solution
  11. dry with materialdried over magnesium sulfate
  12. customevaporated under a reduced pressure
  13. customto remove the solvent
  14. customto remove any unreacted diethyl malonate under a reduced pressure at 140° C.

Sources & evidence

ORD record
ord-3dba68cae81340fdbdeecf122fac98ea
Source dataset
uspto-grants-1992_03
Patent number
US05093370

Reaction notes

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