Isopropanol → HCID 21515707, compound

HRID 1581083Notes

Reaction equation

HRID 1581083 reaction equation
[Na].[CH:2]([OH:5])([CH3:4])[CH3:3].[Br:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]Br>>[Br:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:5][CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 123681,6-DibromohexaneHCID 5360545Sodium2×

Product 1

HCID 21515707HCID 21515707, compound

Procedure

1.15 g (0.05 mol) of finely cut sodium are added to 30 g (0.5 mol) of absolute isopropanol in an atmosphere of nitrogen; the mixture is stirred at 60° for 16 hours in order to dissolve the sodium completely. After cooling to 20°, 12.2 g (0.05 mol) of 1,6-dibromohexane are added and the mixture is stirred at reflux temperature for 18 hours. The precipitated sodium bromide is filtered off, the excess isopropanol is removed and the filtrate is distilled under vacuum. The main fraction (6.0 g), having a B.P. of 96°-98°/15 mm, is chromatographed on 300 g of silica gel with hexane/ethyl acetate (99:1), whereby 1-bromo-6-isopropoxy-hexane is obtained as a colourless oil.

Workup

  1. temperatureAfter cooling to 20°
  2. stirringthe mixture is stirred
  3. temperatureat reflux temperature for 18 hours
  4. filtrationThe precipitated sodium bromide is filtered off
  5. customthe excess isopropanol is removed
  6. distillationthe filtrate is distilled under vacuum
  7. customis chromatographed on 300 g of silica gel with hexane/ethyl acetate (99:1)

Sources & evidence

ORD record
ord-0ee747bf0aac45778f8959c57f428473
Source dataset
uspto-grants-1976_01
Patent number
US03935271

Reaction notes

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