Diethyl Malonate → diethyl 2-cyclohexylmethylmalonate

HRID 1248191Notes

Reaction equation

HRID 1248191 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH:12]1([CH2:18]Br)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>[O-]CC.[Na+]>[CH2:10]([O:9][C:1](=[O:8])[CH:2]([CH2:18][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH3:11]

Participants

4

Reactant 2

HCID 7761Diethyl MalonateHCID 137636Cyclohexane, (bromomethyl)-

Product 1

HCID 599487diethyl 2-cyclohexylmethylmalonateYield 66.4%

Reagents, catalysts & solvents 1

HCID 2723922Sodium ethoxideSolvent

Procedure

Diethyl malonate (16.0 g) was added to a freshly prepared solution of sodium ethoxide (from 2.3 g of sodium in 150 ml of absolute ethanol), followed by 17.7 g of cyclohexylmethyl bromide. The mixture was heated under reflux for four hours and evaporated to dryness. The resulting mixture was treated with water, extracted with ethyl acetate and the extracts washed with water, brine and dried (MgSO4). Evaporation gave an oil which was distilled in vacuo to give 17 g of diethyl(cyclohexylmethyl)malonate (b.p. 104°-107° C. at 0.2 mm Hg).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for four hours
  3. customevaporated to dryness
  4. additionThe resulting mixture was treated with water
  5. extractionextracted with ethyl acetate
  6. washthe extracts washed with water, brine
  7. dry with materialdried (MgSO4)
  8. customEvaporation
  9. customgave an oil which
  10. distillationwas distilled in vacuo

Sources & evidence

ORD record
ord-53f0910570d849d6a8ea5ee573fe74e8
Source dataset
uspto-grants-1985_06
Patent number
US04522948

Reaction notes

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