Propanoic acid, 2-bromo-2-methyl-, ethyl ester → HCID 14871449, compound

HRID 2058076Notes

Reaction equation

HRID 2058076 reaction equation
[Na].[C:2]1([N:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:18]([CH3:25])([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(O)C>[C:2]1([N:8]=[CH:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][C:18]([CH3:25])([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:14][CH:15]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 74319Phenol, 4-[(phenylimino)methyl]-HCID 5360545Sodium

Product 1

HCID 14871449HCID 14871449, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(a) To 170 ml of absolute ethanol is added 1.48 g of sodium, and 8.4 g of 4-(N-phenylformimidoyl)phenol is added to the mixture at room temperature with stirring to prepare a solution. 12.5 g of ethyl 2-bromo-2-methylpropionate is added to the solution, and the mixture is refluxed under heating for 5 hours. After the reaction, the ethanol is distilled off. The residue is dissolved in ether and thereafter washed with 5% aqueous solution of sodium hydroxide and then with water. After drying the resulting mixture, the ether is distilled off to give 9.2 g of ethyl 2-[4-(N-phenylformimidoyl)phenoxy]-2-methylpropionate. Infrared absorption spectrum (liquid film) 1735, 1280, 1245, 1170, 1140, 1020 cm-1.

Workup

  1. additionis added to the mixture at room temperature
  2. customto prepare a solution
  3. temperaturethe mixture is refluxed
  4. temperatureunder heating for 5 hours
  5. customAfter the reaction
  6. distillationthe ethanol is distilled off
  7. dissolutionThe residue is dissolved in ether
  8. washwashed with 5% aqueous solution of sodium hydroxide
  9. customAfter drying the resulting mixture
  10. distillationthe ether is distilled off

Sources & evidence

ORD record
ord-94096d4f017542c5ad3607851d68072a
Source dataset
uspto-grants-1980_07
Patent number
US04214094

Reaction notes

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