Diethyl Ether → HCID 57264773, compound

HRID 2165286Notes

Reaction equation

HRID 2165286 reaction equation
Br[CH2:2][C:3]([O:5][CH:6]([CH2:9][CH3:10])[CH2:7][CH3:8])=[O:4].[Br:11][CH2:12][C:13]([OH:15])=[O:14].[K].CCOCC>CN(C)C=O>[Br:11][CH2:12][C:13]([O:15][CH2:2][C:3]([O:5][CH:6]([CH2:9][CH3:10])[CH2:7][CH3:8])=[O:4])=[O:14]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6227Bromoacetic AcidHCID 347397Pentan-3-yl bromoacetateHCID 5462222Potassium

Product 1

HCID 57264773HCID 57264773, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Bromoacetic acid, 3-pentyl ester (330 g, 1.6 mole) was dissolved in 300 ml of dimethylformamide. Bromoacetic acid, potassium salt (142 g) was added portionwise with stirring and the mixture was stirred overnight. It was then poured into 1 liter of ice-cold water and 500 ml of ether was added. After washing with water, NaHCO3 solution and drying with MgSO4, the ether was evaporated. On distillation 156 g of the starting ester was recovered and 103.5 g of the title compound (boiling point 160°-162° C. at 12 mm of Hg) was obtained.

Workup

  1. stirringthe mixture was stirred overnight
  2. additionwas added
  3. washAfter washing with water, NaHCO3 solution
  4. dry with materialdrying with MgSO4
  5. customthe ether was evaporated
  6. distillationOn distillation 156 g of the starting ester
  7. customwas recovered

Sources & evidence

ORD record
ord-0428b5ce65584491b43c4ab4a788ebe8
Source dataset
uspto-grants-1990_07
Patent number
US04939253

Reaction notes

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