Hydrochloric Acid → HCID 19907382, compound

HRID 2371539Notes

Reaction equation

HRID 2371539 reaction equation
[Na].[C:2]([O:10]CC)(=[O:9])[CH2:3][C:4](OCC)=O.BrC[CH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][CH2:27]Br)=[CH:20][CH:19]=1.Cl>C(O)C.C(O)(=O)C>[C:2]([CH2:3][CH2:27][CH2:26][CH2:25][CH2:24][C:21]1[CH:20]=[CH:19][C:18]([CH2:17][CH2:16][CH2:15][CH2:4][CH2:3][C:2]([OH:10])=[O:9])=[CH:23][CH:22]=1)([OH:10])=[O:9]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 7761Diethyl Malonate2×HCID 5360545SodiumHCID 15284075HCID 15284075, compound

Product 1

HCID 19907382HCID 19907382, compoundYield 68.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

First, 483 mg of metallic sodium was dissolved in 21 ml of absolute ethanol, and after adding dropwise 6.72 g of diethyl malonate under ice-cooling, the mixture was refluxed for 5 minutes. After cooling, a mixture of 3.48 g of 1,4-bis(4-bromobutyl)benzene and 1.12 g of diethyl malonate was added dropwise at a room temperature, and the mixture was refluxed for 50 minutes. To the resulting white suspension, after cooling, 21 ml of ice water was added. The mixture was adjusted to pH 7.0 with 1N hydrochloric acid, and evaporated under a reduced pressure to remove the ethanol. The aqueous layer was twice extracted with 50 ml of benzene, and 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 the remaining diethyl malonate at 140° C. To the colorless oil thus obtained were added 30 ml of acetic acid and 30 ml of concentrated hydrochloric acid, and the mixture was refluxed for 20 hours, and then cooled. The resulting crystal was filtered, washed with water and dried to obtain 2.11 g of the title compound as a colorless crystal.

Workup

  1. temperaturecooling
  2. temperaturethe mixture was refluxed for 5 minutes
  3. temperatureAfter cooling
  4. additionwas added dropwise at a room temperature
  5. temperaturethe mixture was refluxed for 50 minutes
  6. temperatureTo the resulting white suspension, after cooling
  7. customevaporated under a reduced pressure
  8. customto remove the ethanol
  9. extractionThe aqueous layer was twice extracted with 50 ml of benzene
  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. customat 140° C
  15. customTo the colorless oil thus obtained
  16. temperaturethe mixture was refluxed for 20 hours
  17. temperaturecooled
  18. filtrationThe resulting crystal was filtered
  19. washwashed with water
  20. customdried

Sources & evidence

ORD record
ord-a9ea145438884bc69d74e12c42ea9220
Source dataset
uspto-grants-1992_03
Patent number
US05093370

Reaction notes

Loading…