Phenethyl bromide → 1,3-Diethyl 2-(2-phenylethyl)propanedioate

HRID 1732020Notes

Reaction equation

HRID 1732020 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH2:12](Br)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CC[O-].[Na+].[Na]>C(O)C>[CH2:12]([CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 7666Phenethyl bromideHCID 7761Diethyl MalonateHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 811191,3-Diethyl 2-(2-phenylethyl)propanedioate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

45 g of diethyl malonate and 30 g of phenethyl bromide were mixed and added dropwise, cooling in ice, to a solution of sodium ethylate prepared from 6.5 g of sodium and 130 ml of absolute ethanol. The mixture was then boiled under reflux for 6 hours and allowed to cool down overnight. The major part of the ethanol was removed in vacuo, the residue was taken up in water, extracted with ether, this was dried over Na2SO4, evaporated and distilled.

Workup

  1. additionadded dropwise
  2. temperatureunder reflux for 6 hours
  3. temperatureto cool down overnight
  4. customThe major part of the ethanol was removed in vacuo
  5. extractionextracted with ether
  6. dry with materialthis was dried over Na2SO4
  7. customevaporated
  8. distillationdistilled

Sources & evidence

ORD record
ord-806afa771f5246778a4f85b4d90eeb8e
Source dataset
uspto-grants-1986_11
Patent number
US04624962

Reaction notes

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