1,6-Dibromohexane → 1-Bromo-6-isopentyloxy hexane

HRID 1284176Notes

Reaction equation

HRID 1284176 reaction equation
[H-].[Na+].[CH2:3]([OH:8])[CH2:4][CH:5]([CH3:7])[CH3:6].[Br:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]Br>>[Br:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:8][CH2:3][CH2:4][CH:5]([CH3:7])[CH3:6]

Participants

4

Reactant 3

HCID 123681,6-DibromohexaneHCID 24758Sodium hydrideHCID 31260Isoamyl Alcohol

Product 1

HCID 214340381-Bromo-6-isopentyloxy hexane

Procedure

4.8 g (0.11 mol) of 55 % sodium hydride dispersion are added at 20°-40°C over the course of 1 hour, to 74 g (1.0 mol) of isopentyl alcohol. After stirring for 2 hours at 20°-25°C, 24.4 g (0.10 mol) of 1,6-dibromohexane are added dropwise over the course of 15 minutes. The mixture is stirred at 60°C for 16 hours, then filtered and the filtrate is taken up in ether. The ether solution is extracted with saturated sodium chloride slution, dried with sodium sulphate and evaporated at 40°C/18 mm Hg. After chromatography of the residue on silica gel with hexane/ethyl acetate (99:1) and subsequent distillation (B.P. 85°-87°/1 mm), 1-bromo-6-isopentyloxy-hexane is obtained as a slightly yellow clear liquid.

Workup

  1. stirringThe mixture is stirred at 60°C for 16 hours
  2. filtrationfiltered
  3. extractionThe ether solution is extracted with saturated sodium chloride slution
  4. dry with materialdried with sodium sulphate
  5. customevaporated at 40°C/18 mm Hg
  6. distillationAfter chromatography of the residue on silica gel with hexane/ethyl acetate (99:1) and subsequent distillation (B.P. 85°-87°/1 mm)

Sources & evidence

ORD record
ord-be7f6757b2d4413eadc5d66a130cba00
Source dataset
uspto-grants-1976_08
Patent number
US03978097

Reaction notes

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