Propanoic acid, 2-bromo-2-methyl-, ethyl ester → HCID 20329874, compound

HRID 2058083Notes

Reaction equation

HRID 2058083 reaction equation
[Na].[C:2]1([CH3:17])[CH:7]=[CH:6][C:5]([N:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.Br[C:19]([CH3:26])([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(O)C>[C:2]1([CH3:17])[CH:3]=[CH:4][C:5]([N:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:19]([CH3:26])([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:12][CH:11]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 6111664-{(E)-[(4-methylphenyl)imino]methyl}phenolHCID 5360545Sodium

Product 1

HCID 20329874HCID 20329874, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(a) To 50 ml of absolute ethanol is added 0.58 g of sodium, and 4.2 g of 4-[N-(p-tolyl)formimidoyl]phenol and then 7.84 g of ethyl 2-bromo-2-methylpropionate are added to the solution at room temperature with stirring. The mixture is refluxed under heating and with stirring for 5 hours on an oil bath. After distilling off the ethanol from the reaction mixture, the residue is dissolved in ether. The solution is washed with 5% aqueous solution of sodium hydroxide and then with water. After drying the solution, the ether is distilled off, and the residue is further concentrated under reduced pressure on an oil bath at 100° C. to give 4.0 g of ethyl 2-[4-{N-(p-tolyl)formimidoyl}phenoxy]-2-methylpropionate as an oily product.

Workup

  1. temperatureThe mixture is refluxed
  2. temperatureunder heating
  3. stirringwith stirring for 5 hours on an oil bath
  4. distillationAfter distilling off the ethanol from the reaction mixture
  5. dissolutionthe residue is dissolved in ether
  6. washThe solution is washed with 5% aqueous solution of sodium hydroxide
  7. customAfter drying the solution
  8. distillationthe ether is distilled off
  9. concentrationthe residue is further concentrated under reduced pressure on an oil bath at 100° C.

Sources & evidence

ORD record
ord-67ed7e337b5847bba5f361e2a1d148d5
Source dataset
uspto-grants-1980_07
Patent number
US04214094

Reaction notes

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