Hydrochloric Acid → Diethyl 2-(benzyloxyhexyl)malonate

HRID 1289381Notes

Reaction equation

HRID 1289381 reaction equation
[O-]CC.[Na+].[C:5]([O:13][CH2:14][CH3:15])(=[O:12])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl>C(O)C>[CH2:24]([O:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:5]([O:13][CH2:14][CH3:15])=[O:12])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 2723922Sodium ethoxideHCID 2784764Benzyl 6-Bromohexyl Ether

Product 1

HCID 10383239Diethyl 2-(benzyloxyhexyl)malonateYield 98.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

First, 2.7 g of sodium ethoxide and 100 ml of dry ethanol were placed in a 200 ml flask. Then, 20 ml of an ethanol solution containing 7 g of diethyl malonate was added dropwise to the reaction mixture at 60° C., and the resultant reaction mixture was stirred for 2 hours. Then, 20 ml of an ethanol solution containing 9 g of 1-bromo-6-benzyloxyhexane was added dropwise to the reaction mixture, and the resultant reaction mixture was stirred under reflux for 3 hours. The reaction mixture was poured into diluted hydrochloric acid, and an organic layer was extracted with ether. The ether layer was washed with water and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1) to obtain 11.5 g of diethyl 2-(6-benzyloxyhexyl)malonate (Y: 98%). The compound thus obtained had a purity of 86.3% by GC.

Workup

  1. additionwas added dropwise to the reaction mixture at 60° C.
  2. customthe resultant reaction mixture
  3. additionwas added dropwise to the reaction mixture
  4. customthe resultant reaction mixture
  5. stirringwas stirred
  6. temperatureunder reflux for 3 hours
  7. extractionan organic layer was extracted with ether
  8. washThe ether layer was washed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationThereafter, the solvent was distilled away
  11. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-30d98b85f04f450095a314292c4d698c
Source dataset
uspto-grants-1998_05
Patent number
US05750213

Reaction notes

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