1,4-Dibromobutane → 1-Bromo-4-(4-isopentyloxy-butyloxy)-butane

HRID 2398789Notes

Reaction equation

HRID 2398789 reaction equation
[H-].[Na+].[CH2:3]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[CH2:4][CH:5]([CH3:7])[CH3:6].[Br:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.[Br-].[Na+]>>[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][O:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][CH2:3][CH2:4][CH:5]([CH3:7])[CH3:6]

Participants

5

Reactant 4

HCID 80561,4-DibromobutaneHCID 24758Sodium hydrideHCID 253881Sodium BromideHCID 137211974-Isopentyloxy butanol

Product 1

HCID 214340441-Bromo-4-(4-isopentyloxy-butyloxy)-butane

Procedure

1.77 g (0.041 mol) of 55% sodium hydride dispersion in oil are carefully added over the course of 40 minutes, under nitrogen and while stirring, to 26.0 g (0.163 mol) of 4-isopentyloxy-butanol. The mixture is stirred at 60° for 30 minutes and 11.4 g (0.053 mol) of 1,4-dibromobutane are subsequently added dropwise and it is stirred at 60° for 20 hours. The resulting sodium bromide is suction filtered, washed with ether and the filtrate is evaporated. The residue is fractionally distilled in a high vacuum and apart from the excess 4-isopentyloxy butanol, 1-bromo-4-(4-isopentyloxy-butyloxy)-butane, having a B.P. of 121-123°/0.7 mm Hg, is obtained as a colourless liquid.

Workup

  1. stirringit is stirred at 60° for 20 hours
  2. filtrationfiltered
  3. washwashed with ether
  4. customthe filtrate is evaporated
  5. distillationThe residue is fractionally distilled in a high vacuum and apart from the excess 4-isopentyloxy butanol, 1-bromo-4-(4-isopentyloxy-butyloxy)-butane
  6. customis obtained as a colourless liquid

Sources & evidence

ORD record
ord-eba175143484426abc47abcd60b1bb64
Source dataset
uspto-grants-1977_05
Patent number
US04025641

Reaction notes

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