Water → 1-[4-[(6-Bromohexyl)oxy]butyl]benzene

HRID 893762Notes

Reaction equation

HRID 893762 reaction equation
[H-].[Na+].[C:3]1([CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]Br.O>C1COCC1>[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:13][CH2:12][CH2:11][CH2:10][CH2:9][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 123681,6-DibromohexaneHCID 24758Sodium hydrideHCID 76889Benzenebutanol

Product 1

HCID 110124391-[4-[(6-Bromohexyl)oxy]butyl]benzeneYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (46% dispersion in oil; 6.5 g) was added portion wise to a solution of 4-phenyl-1-butanol (15.0 g) and 1,6-dibromohexane (48.8 g) in THF (200 ml) under nitrogen. The resulting suspension was refluxed for 27 h and treated with H2O (80 ml). The mixture was extracted with ER (2×200 ml) and The dried extract was evaporated to leave a orange oil. The oil was purified on a column of silica (800 ml) [A] to give a yellow oil on which distillation gave the title compound as a colorless oil (15.0 g) b.p. 90°-95°/0.1 mm Hg.

Workup

  1. temperatureThe resulting suspension was refluxed for 27 h
  2. extractionThe mixture was extracted with ER (2×200 ml)
  3. extractionThe dried extract
  4. customwas evaporated
  5. customto leave a orange oil
  6. customThe oil was purified on a column of silica (800 ml) [A]
  7. customto give a yellow oil
  8. distillationon which distillation

Sources & evidence

ORD record
ord-e1dc8a239cda400e8d9ccf16b6cacc70
Source dataset
uspto-grants-1992_06
Patent number
US05126375

Reaction notes

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