Water → [(2-[(6-Bromohexyl)oxy]ethoxy)methyl]benzene

HRID 2116939Notes

Reaction equation

HRID 2116939 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].O.[Br:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]Br>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:11][CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 121412-(Benzyloxy) ethanolHCID 123681,6-DibromohexaneHCID 14798Sodium Hydroxide

Product 1

HCID 46833105[(2-[(6-Bromohexyl)oxy]ethoxy)methyl]benzene

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

A solution of 2-(benzyloxy)ethanol (2.00 g) and tetrabutylammonium bromide (84 mg) in 1,6-dibromohexane (6.06 ml) was treated with 50% w/v sodium hydroxide solution (5.0 ml) and the mixture was vigorously stirred for 18 h at 20°. Water (50 ml) was added and the mixture was extracted with dichloromethane (40 ml). The organic extract was dried (Na2SO4) and the solvent evaporated in vacuo to give a residue which was purified by flash chromatography on silica gel. Elution with EtOAc-PE (1:9) gave the title compound (2.87 g). LCMS RT=3.94 min, ES+ve 337 (MNa)+, 339 (MNa)+

Workup

  1. extractionthe mixture was extracted with dichloromethane (40 ml)
  2. extractionThe organic extract
  3. dry with materialwas dried (Na2SO4)
  4. customthe solvent evaporated in vacuo
  5. customto give a residue which
  6. customwas purified by flash chromatography on silica gel
  7. washElution with EtOAc-PE (1:9)

Sources & evidence

ORD record
ord-e9221a9605dc4e3d9c5a70a68cb2a923
Source dataset
uspto-grants-2008_10
Patent number
US07439393B2

Reaction notes

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