Diethyl Ether → HCID 12603088, compound

HRID 330308Notes

Reaction equation

HRID 330308 reaction equation
BrC[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[Br:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1C=O.CC[O:21][CH2:22][CH3:23]>C1COCC1>[Br:10][C:11]1[CH:18]=[CH:17][C:16]([CH:22]([OH:21])[CH2:23][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH3:3])=[CH:15][CH:12]=1

Participants

5

Reactant 3

HCID 3283Diethyl Ether3×HCID 81401-BromooctaneHCID 811292-Bromobenzaldehyde

Product 1

HCID 12603088HCID 12603088, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a 100 ml round bottom flask with a Y adapter, condensor, and a 10 ml addition funnel was added 0.38 g (15.63 mmol) of Mg turnings which had been ground with a mortar and pestle. The apparatus was then flushed with argon and flame dried. After allowing the apparatus to cool under arqon, 4 ml of anhydrous diethyl either was added to the Mg. While vigorously stirring the Mg in the ether, 2.52 g (13.05 mmol) of 1-bromooctane in 3 ml of diethyl ether was added dropwise. After 5 drops, the Grignard reaction started and the addition was continued at a rate sufficient to maintain a steady reflux. After addition was complete, 4 ml of dry THF was added to the Grignard reagent and it was stirred at R.T. for an additional 1/2 hour. A warm water bath was then placed under the flask, and refluxing was continued for 15 minutes. Afterwards, the reaction was cooled to 0° C. with an ice bath and 2.00 g (16.81 mmol) of p bromobenzaldehyde in 4 ml of the THF was added. The reaction was stirred at R.T. for 1.5 hrs., whereupon the Grignard was quenched with saturated NH4Cl. The organic layer was washed with H2O and brine, then dried (MgSO4). Rotary evaporation of the solvent under reduced pressure produced 2.96 g of a crude yellow oil. The oil was dissolved in a diethyl ether and loaded onto a silica gel column. Elution with diethyl ether/hexane yielded 2.22 g of the titled product as a yellow oil.

Workup

  1. additionIn a 100 ml round bottom flask with a Y adapter, condensor, and a 10 ml addition funnel
  2. customThe apparatus was then flushed with argon
  3. temperatureflame
  4. customdried
  5. temperatureto cool under arqon, 4 ml of anhydrous diethyl
  6. additionwas added to the Mg
  7. additionwas added dropwise
  8. customAfter 5 drops, the Grignard reaction
  9. additionthe addition
  10. temperatureto maintain a steady reflux
  11. additionAfter addition
  12. customA warm water bath was then placed under the flask
  13. temperaturerefluxing
  14. waitwas continued for 15 minutes
  15. temperatureAfterwards, the reaction was cooled to 0° C. with an ice bath
  16. stirringThe reaction was stirred at R.T. for 1.5 hrs
  17. custom, whereupon the Grignard was quenched with saturated NH4Cl
  18. washThe organic layer was washed with H2O and brine
  19. dry with materialdried (MgSO4)
  20. customRotary evaporation of the solvent under reduced pressure
  21. customproduced 2.96 g of a crude yellow oil
  22. washElution with diethyl ether/hexane

Sources & evidence

ORD record
ord-4ddf5945c6964d99a83daf9f84c33dca
Source dataset
uspto-grants-1990_01
Patent number
US04895869

Reaction notes

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