Hydrochloric Acid → Diethyl (4-chlorobutyl)propanedioate

HRID 1794228Notes

Reaction equation

HRID 1794228 reaction equation
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Br[CH2:15][CH2:16][CH2:17][CH2:18][Cl:19].Cl>O1CCCC1>[Cl:19][CH2:18][CH2:17][CH2:16][CH2:15][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][CH2:12][CH3:13])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 813641-Bromo-4-chlorobutane

Product 1

HCID 53401795Diethyl (4-chlorobutyl)propanedioateYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 458 ml of dry tetrahydrofuran (THF) was added 13.4 g of 60% sodium hydride, and 160.6 g of diethyl malonate was added dropwise with stirring under ice-cooling. After addition, stirring was continued for 15 minutes, and 57.3 g of 1-bromo-4-chlorobutane was added. The mixture was stirred for 50 hours at room temperature. The reaction solution was poured into ice-cold water, neutralized with dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was distilled under reduced pressure to provide 26.8 g of the objective compound as colorless oil. B.p. 127–130° C. (5 mmHg).

Workup

  1. additionwas added dropwise
  2. temperaturecooling
  3. additionAfter addition
  4. stirringstirring
  5. stirringThe mixture was stirred for 50 hours at room temperature
  6. additionThe reaction solution was poured into ice-cold water
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated
  11. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-0aa322b3242b4737a07d88ea0d0d0cf5
Source dataset
uspto-grants-2006_04
Patent number
US07022723B2

Reaction notes

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