Benzyl Bromide → HCID 178520957, compound

HRID 1456348Notes

Reaction equation

HRID 1456348 reaction equation
[H-].[Na+].[OH:3][CH2:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][OH:12])[CH2:7][CH2:6]1.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCCC1>[CH2:13]([O:3][CH2:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][OH:12])[CH2:7][CH2:6]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178520956HCID 178520956, compound

Product 1

HCID 178520957HCID 178520957, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 10 ml of tetrahydrofuran was suspended 1.51 g of sodium hydride (55% content), and a solution of 5.0 g of trans-1,4-dihydroxymethylcyclohexane dissolved in 20 ml of tetrahydrofuran was added dropwise thereto with stirring under ice-cooling, and the reaction mixture was stirred at room temperature for 50 minutes. To the reaction mixture was added 3.79 ml of benzyl bromide with stirring under ice-cooling and the mixture was stirred under ice-cooling for 1 hour and further at room temperature overnight. The insolubles were separated by filtration and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, and the solution was washed successively with an aqueous sodium chloride solution, 10% aqueous hydrochloric acid solution, an aqueous sodium chloride solution and an aqueous sodium bicarbonate solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: cyclohexane/ethyl acetate=20/1-5/1) to obtain 1.75 g of the desired compound as a colorless oil.

Workup

  1. additionwas added dropwise
  2. temperaturecooling
  3. stirringthe reaction mixture was stirred at room temperature for 50 minutes
  4. stirringwith stirring under ice-
  5. temperaturecooling
  6. stirringthe mixture was stirred under ice-
  7. customThe insolubles were separated by filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. dissolutionThe residue was dissolved in ethyl acetate
  10. washthe solution was washed successively with an aqueous sodium chloride solution, 10% aqueous hydrochloric acid solution
  11. dry with materialan aqueous sodium chloride solution and an aqueous sodium bicarbonate solution and dried over anhydrous magnesium sulfate
  12. distillationThe solvent was distilled off under reduced pressure
  13. customThe residue was purified by silica gel column chromatography (eluting solvent: cyclohexane/ethyl acetate=20/1-5/1)

Sources & evidence

ORD record
ord-83829b496d8b4c718b76e26f733db8d6
Source dataset
uspto-grants-1998_12
Patent number
US05843973

Reaction notes

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