Diethyl Malonate → Diethyl octylmalonate

HRID 2050134Notes

Reaction equation

HRID 2050134 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C[O-].[Na+].[C:13]([O:21][CH2:22][CH3:23])(=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>CO>[CH2:1]([CH:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:13]([O:21][CH2:22][CH3:23])=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 81401-BromooctaneHCID 10942334Sodium Methoxide

Product 1

HCID 252340Diethyl octylmalonateYield 66.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

n-Octylbromide (193 g, 1 m) was slowly added to a mixture of 25% sodium methoxide solution (216 g, 1 m), diethyl malonate (160 g, 1 m) and methanol (1 l) with stirring at room temperature. The resulting mixture was refluxed until neutral to litmus (about 24 hours). The solvent was stripped off and the residue was filtered and washed with chloroform. The filtrate was evaporated to remove chloroform and the residue was vacuum-distilled to yield diethyl n-octylmalonate (180 g, 66%) bp 105°-115° C./0.5-0.7 mm.

Workup

  1. temperatureThe resulting mixture was refluxed until neutral to litmus (about 24 hours)
  2. filtrationthe residue was filtered
  3. washwashed with chloroform
  4. customThe filtrate was evaporated
  5. customto remove chloroform
  6. distillationthe residue was vacuum-distilled

Sources & evidence

ORD record
ord-0539de420acf464eb5b3555fea56a8b0
Source dataset
uspto-grants-1980_04
Patent number
US04200580

Reaction notes

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