(+-)-2-Butanol → HCID 21515713, compound

HRID 1284177Notes

Reaction equation

HRID 1284177 reaction equation
[CH:1]([OH:5])([CH2:3][CH3:4])[CH3:2].[Na].[Br:7][CH2:8][CH2:9][CH:10]([CH3:14])[CH2:11][CH2:12]Br>>[Br:7][CH2:8][CH2:9][CH:10]([CH3:14])[CH2:11][CH2:12][O:5][CH:1]([CH2:3][CH3:4])[CH3:2]

Participants

4

Reactant 3

HCID 6568(+-)-2-ButanolHCID 1382581,5-Dibromo-3-methylpentaneHCID 5360545Sodium2×

Product 1

HCID 21515713HCID 21515713, compound

Procedure

To 115 g (1.56 mols) of sec-butanol are added over the course of 15 minutes, 2.0 g (0.087 mol) of finely cut sodium. The mixture is stirred at 60° for 2 hours in order to dissolve the sodium completely. After the addition of 21.2 g (0.087 mol) of 1,5-dibromo-3-methylpentane, the mixture is stirred at 60°, over the source of 18 hours. The precipitated sodium bromide is filtered off and the excess sec-butanol is distilled off. The residue is taken up in 300 cc of ether, washed three times with water and once with saturated sodium chloride solution, dried over magnesium sulphate and evaporated at 40° /20 mm Hg. After chromatography of the residue on silica gel with hexane/ethyl acetate (98,5:1,5) and subsequent fractional distillation in a high vacuum, 1-bromo-5-sec-butoxy-3-methyl-pentane is obtained as a colourless liquid. B.P.: 104° - 106°/13 mm Hg

Workup

  1. stirringthe mixture is stirred at 60°, over the source of 18 hours
  2. filtrationThe precipitated sodium bromide is filtered off
  3. distillationthe excess sec-butanol is distilled off
  4. washwashed three times with water
  5. dry with materialonce with saturated sodium chloride solution, dried over magnesium sulphate
  6. customevaporated at 40° /20 mm Hg
  7. distillationAfter chromatography of the residue on silica gel with hexane/ethyl acetate (98,5:1,5) and subsequent fractional distillation in a high vacuum

Sources & evidence

ORD record
ord-a0bf531453d64ec5ac463ac6a1d3c18b
Source dataset
uspto-grants-1976_08
Patent number
US03978097

Reaction notes

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