Ethyl bromoacetate → Ethyl 3-acetyl-4-oxopentanoate

HRID 1375095Notes

Reaction equation

HRID 1375095 reaction equation
[OH-].[K+].[CH3:3][C:4](=[O:9])[CH2:5][C:6](=[O:8])[CH3:7].O1CCOCC1.[CH2:16]([O:18][C:19](=[O:22])[CH2:20]Br)[CH3:17]>O>[CH2:16]([O:18][C:19](=[O:22])[CH2:20][CH:5]([C:4](=[O:9])[CH3:3])[C:6](=[O:8])[CH3:7])[CH3:17]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 14797Potassium HydroxideHCID 31261AcetylacetoneHCID 312751,4-Dioxane

Product 1

HCID 87820Ethyl 3-acetyl-4-oxopentanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

28 g of potassium hydroxide dissolved in 28 ml of water was added to a mixture of 50 g of 2,4-pentandione, and 100 ml and 115 ml of dioxane at 0 to 10° C. After 20 minutes of stirring, 125 g of bromoacetic acid ethyl ester was added dropwise and the mixture was stirred for 19 hours. The layers were separated and washed with water and diethyl ether. The organic layer was dried and 3-acetyl-4-oxo-pentanoic acid ethyl ester was isolated by fractional distillation.

Workup

  1. stirringthe mixture was stirred for 19 hours
  2. customThe layers were separated
  3. washwashed with water and diethyl ether
  4. customThe organic layer was dried

Sources & evidence

ORD record
ord-1578fc02c3994d76898e4ee5b766e417
Source dataset
uspto-grants-2007_01
Patent number
US07166648B2

Reaction notes

Loading…