Benzyl Alcohol → Benzyl 6-Bromohexyl Ether

HRID 260820Notes

Reaction equation

HRID 260820 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br>O1CCOCC1>[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:10][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 123681,6-DibromohexaneHCID 24758Sodium hydride

Product 1

HCID 2784764Benzyl 6-Bromohexyl Ether

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent3×

Procedure

To a suspension of sodium hydride in 1,4-dioxane was added benzyl alcohol in 1,4-dioxane over a period of 30 minutes at 80° C., and the mixture was stirred for 1 hour. The obtained alkoxide solution was added to a solution of 1,6-dibromohexane in 1,4-dioxane at room temperature. The mixture was stirred at 80° C. for 14 hours and insoluble materials were filtered off. The filtrate was concentrated and the residue was distilled under reduced pressure to give the object compound.

Workup

  1. stirringThe mixture was stirred at 80° C. for 14 hours
  2. filtrationinsoluble materials were filtered off
  3. concentrationThe filtrate was concentrated
  4. distillationthe residue was distilled under reduced pressure
  5. customto give the object compound

Sources & evidence

ORD record
ord-9d1d155b2a884e578db41fc4e08d3656
Source dataset
uspto-grants-1996_06
Patent number
US05530019

Reaction notes

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