Diethyl Malonate → Diethyl octylmalonate

HRID 1197380Notes

Reaction equation

HRID 1197380 reaction equation
[Na].[O-]CC.[Na+].[C:6]([O:14][CH2:15][CH3:16])(=[O:13])[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH2:17](Br)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>C(O)C>[CH2:17]([CH:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:6]([O:14][CH2:15][CH3:16])=[O:13])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 7761Diethyl MalonateHCID 81401-BromooctaneHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 252340Diethyl octylmalonateYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

200 ml of ethanol was put in a 1-liter four-necked flask, 7.6 g of metal sodium cut into pieces was put therein portionwise to prepare sodium ethoxide. To this were added dropwise 54.6 g of diethyl malonate and then 63.9 g of octyl bromide. Thereafter, the mixture was refluxed for 3 hours. Then, the most part of ethanol was distilled away under the atmospheric pressure, 200 ml of water was added, and the mixture was extracted with 250 ml of ether. The ether solution was dried over sodium sulfate, ether was distilled away, and the residue was distilled under reduced pressure to give 72.1 g of a colorless oily substance (b.p. 111° C./2 mmHg). Yield 85%.

Workup

  1. temperatureThereafter, the mixture was refluxed for 3 hours
  2. distillationThen, the most part of ethanol was distilled away under the atmospheric pressure, 200 ml of water
  3. additionwas added
  4. extractionthe mixture was extracted with 250 ml of ether
  5. dry with materialThe ether solution was dried over sodium sulfate, ether
  6. distillationwas distilled away
  7. distillationthe residue was distilled under reduced pressure
  8. customto give 72.1 g of a colorless oily substance (b.p. 111° C./2 mmHg)

Sources & evidence

ORD record
ord-abde6d6b9f8449fe9939e32931269203
Source dataset
uspto-grants-1994_01
Patent number
US05275757

Reaction notes

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