Diethyl Malonate → Diethyl 4-propylcyclohexylmalonate

HRID 1707527Notes

Reaction equation

HRID 1707527 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].[CH2:13]([CH:16]1[CH2:21][CH2:20][CH:19](Br)[CH2:18][CH2:17]1)[CH2:14][CH3:15]>C(O)C>[CH2:13]([CH:16]1[CH2:21][CH2:20][CH:19]([CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]([O:10][CH2:11][CH3:12])=[O:9])[CH2:18][CH2:17]1)[CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 5360545SodiumHCID 140472411-Bromo-4-propylcyclohexane

Product 1

HCID 13561188Diethyl 4-propylcyclohexylmalonateYield 43.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

31 g (1.35 mol) of sodium was dissolved in 660 cm3 of anhydrous ethanol, after which 216 g (1.35 mol) of diethyl malonate and then 180 g (0.88 mol) of 4-propylbromocyclohexane were added in single additions, and it was refluxed for 10 hours on a hot water bath. The reactant was cooled to room temperature, and after filtering the NaBr crystals that had formed, the ethanol in the filtrate was removed. Water was added to the residue, it was extracted with chloroform, and washed with water. The chloroform was removed, and the remaining oily substance was distilled under reduced pressure (b. p. 138° C./1.4 mmHg) to obtain 108 g (0.38 mol) of diethyl 4-propylcyclohexylmalonate (trans-cis form mixture).

Workup

  1. temperaturewas refluxed for 10 hours on a hot water bath
  2. filtrationafter filtering the NaBr crystals that
  3. customhad formed
  4. customthe ethanol in the filtrate was removed
  5. additionWater was added to the residue, it
  6. extractionwas extracted with chloroform
  7. washwashed with water
  8. customThe chloroform was removed
  9. distillationthe remaining oily substance was distilled under reduced pressure (b. p. 138° C./1.4 mmHg)

Sources & evidence

ORD record
ord-81e3a67396e44c6f8c2e085f382d1295
Source dataset
uspto-grants-1994_10
Patent number
US05354502

Reaction notes

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