Propanoic acid, 2-bromo-2-methyl-, ethyl ester → HCID 20329847, compound

HRID 2058080Notes

Reaction equation

HRID 2058080 reaction equation
[Na].[CH:2]1([N:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.Br[C:18]([CH3:25])([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(O)C>[CH:2]1([N:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:18]([CH3:25])([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:12][CH:11]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 2412384-[(Cyclohexylimino)methyl]phenolHCID 5360545Sodium

Product 1

HCID 20329847HCID 20329847, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(a) To 70 ml of absolute ethanol is added 872 mg of sodium, and 7 g of 4-(N-cyclohexylformimidoyl)phenol is added to the solution. Subsequently, 7.4 g of ethyl 2-bromo-2-methylpropionate is further added. The mixture is refluxed under heating and with stirring for 15 hours. After distilling off the ethanol from the reaction mixture, water is added to the residue, and the solution is extracted three times with benzene. The extract is washed with water twice, with cooled dilute aqueous solution of sodium hydroxide three times and then with water twice. After drying the resulting solution over magnesium sulfate, the solvent is distilled off to give 5.54 g of ethyl 2-[4-(N-cyclohexylformimidoyl)phenoxy]-2-methylpropionate as an oil.

Workup

  1. additionis added to the solution
  2. temperatureThe mixture is refluxed
  3. temperatureunder heating
  4. distillationAfter distilling off the ethanol from the reaction mixture, water
  5. additionis added to the residue
  6. extractionthe solution is extracted three times with benzene
  7. washThe extract is washed with water twice
  8. temperaturewith cooled dilute aqueous solution of sodium hydroxide three times
  9. dry with materialAfter drying the resulting solution over magnesium sulfate
  10. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-ab3ae68d7a6e40e59afeed458ea3b612
Source dataset
uspto-grants-1980_07
Patent number
US04214094

Reaction notes

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