Ethanol → HCID 20329877, compound

HRID 2058082Notes

Reaction equation

HRID 2058082 reaction equation
C(O)C.[Na].[CH2:5]([N:12]=[CH:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Br[C:22]([CH3:29])([CH3:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24]>O>[CH2:5]([N:12]=[CH:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][C:22]([CH3:29])([CH3:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:18][CH:19]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 792803HCID 792803, compoundHCID 5360545Sodium

Product 1

HCID 20329877HCID 20329877, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(a) To 50 ml of absolute ethanol is added 0.573 g of sodium, and 5 g of 4-(N-benzylformimidoyl)phenol and then 5.54 g of ethyl 2-bromo-2-methylpropionate are added to the solution under cooling with water. The mixture is refluxed under heating and with stirring for 22 hours. The ethanol is distilled off from the reaction mixture under reduced pressure. After dissolving the residue in 30 ml of benzene, the insolubles are filtered off. The benzene filtrate is washed with water twice, then dried over magnesium sulfate and thereafter the solvent is distilled off. 6.12 g of the resulting oily product is dissolved in ether. After removing the insolubles from the ethereal solution by filtration, the filtrate is concentrated to give 5.06 g of ethyl 2-[4-(N-benzylformimidoyl)phenoxy]-2-methylpropionate in the form of a pale brown oil.

Workup

  1. temperatureThe mixture is refluxed
  2. temperatureunder heating
  3. distillationThe ethanol is distilled off from the reaction mixture under reduced pressure
  4. dissolutionAfter dissolving the residue in 30 ml of benzene
  5. filtrationthe insolubles are filtered off
  6. washThe benzene filtrate is washed with water twice
  7. dry with materialdried over magnesium sulfate
  8. distillationthe solvent is distilled off
  9. dissolution6.12 g of the resulting oily product is dissolved in ether
  10. customAfter removing the insolubles from the ethereal solution
  11. filtrationby filtration
  12. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-4faa876c865142d9bce70ad3a8a42979
Source dataset
uspto-grants-1980_07
Patent number
US04214094

Reaction notes

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