Water → 2-[2-[(6-Bromohexyl)oxy]ethyl]-1,3-dimethylbenzene

HRID 483467

Reaction equation

HRID 483467 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[CH2:11][CH2:12][OH:13].[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][C:5]1[C:6]([CH3:10])=[CH:7][CH:8]=[CH:9][C:4]=1[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 123681,6-DibromohexaneHCID 24758Sodium hydrideHCID 339422-(2,6-Dimethylphenyl)ethanol

Product 1

HCID 133756312-[2-[(6-Bromohexyl)oxy]ethyl]-1,3-dimethylbenzeneYield 52.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (46% dispersion in oil; 4.2 g) was added portionwise to a solution of 2,6-dimethylbenzenethanol (6.0 g) and 1,6-dibromohexane (19.52 g) in THF (50 ml) under nitrogen. The mixture was refluxed for 18 h and treated cautiously with H2O (20 ml). The resulting emulsion was extracted with ER (3×100 ml) and the dried extract was evaporated to leave a yellow oil. Excess 1,6-dibromohexane was removed under reduced pressure and the residue was purified on a column of silica (300 ml) [B] to give the title compound as a colourless oil (6.6 g) b.p. 110°-115°/0.4 mmHg.

Workup

  1. temperatureThe mixture was refluxed for 18 h
  2. extractionThe resulting emulsion was extracted with ER (3×100 ml)
  3. extractionthe dried extract
  4. customwas evaporated
  5. customto leave a yellow oil
  6. customExcess 1,6-dibromohexane was removed under reduced pressure
  7. customthe residue was purified on a column of silica (300 ml) [B]

Sources & evidence

ORD record
ord-b45e9f33fcc441fbb18d0d192db745b3
Source dataset
uspto-grants-1993_07
Patent number
US05225445

Linked notes

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