Benzyl Chloride → Diethyl dibenzylpropanedioate

HRID 2170725Notes

Reaction equation

HRID 2170725 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[CH2:14](Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[NH4+]>CN(C)C=O>[CH2:14]([C:2]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 7503Benzyl ChlorideHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 25517Ammonium Chloride

Product 1

HCID 222519Diethyl dibenzylpropanedioateYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Diethyl malonate (4.53 mL, 30.0 mmol) was added gradually at 0° C. to a mixed liquid containing sodium hydride (55 wt % in oil, 2.95 g, 67.5 mmol) and anhydrous N,N-dimethylformamide (60 mL). Following stirring of the resulting mixed liquid at this temperature for 30 minutes, benzyl chloride (7.25 mL, 63.0 mmol) was added. The resulting mixed liquid was stirred at room temperature for one hour, and a saturated aqueous solution of ammonium chloride was then added to halt the reaction. The organic layer was separated from the mixed liquid, and the water layer was extracted with ethyl acetate. The thus obtained organic layer was washed with a saturated saline solution and then dried using anhydrous magnesium sulfate, yielding the title compound (1a-1) in a yield of 95%.

Workup

  1. additionmixed liquid at this temperature for 30 minutes
  2. additionThe resulting mixed liquid
  3. stirringwas stirred at room temperature for one hour
  4. customthe reaction
  5. customThe organic layer was separated from the mixed liquid
  6. extractionthe water layer was extracted with ethyl acetate
  7. washThe thus obtained organic layer was washed with a saturated saline solution
  8. customdried

Sources & evidence

ORD record
ord-aea54cca04ff463cb3fa4b16512e06df
Source dataset
uspto-grants-2015_06
Patent number
US09051246B2

Reaction notes

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