Ethyl Bromide → Butanoic acid, 2-ethyl-3-oxo-, methyl ester

HRID 5624

Reaction equation

HRID 5624 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[CH2:9](Br)[CH3:10].C[O-].[Na+]>CO>[C:3]([CH:2]([CH2:9][CH3:10])[C:1]([O:7][CH3:8])=[O:6])(=[O:4])[CH3:5]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 7757Methyl acetoacetateHCID 10942334Sodium Methoxide

Product 1

HCID 103534Butanoic acid, 2-ethyl-3-oxo-, methyl esterYield 56.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

465 g of methyl acetoacetate and then 458 g of ethyl bromide were added under nitrogen to 720 g of 30% sodium methylate solution in 1200 ml of methanol. The reaction mixture was subsequently boiled at reflux. After distillation of the methanol the residue was poured on to ice-water. It was then extracted with n-hexane and water. The organic phases were combined and dried. After evaporation of the solvent and distillation there were obtained 328 g (56.9%) of methyl 2-acetylbutyrate, b.p. 77°-79°/15 Torr.

Workup

  1. temperatureat reflux
  2. distillationAfter distillation of the methanol the residue
  3. additionwas poured on to ice-water
  4. extractionIt was then extracted with n-hexane and water
  5. customdried
  6. customAfter evaporation of the solvent
  7. distillationdistillation there

Sources & evidence

ORD record
ord-f9b363bf630049efa482b18098a1d4e7
Source dataset
uspto-grants-1993_09
Patent number
US05245056

Linked notes

Loading…