Diethyl Ether → 6-(4-Isopentyloxybutyloxy)-hexanol

HRID 2398792Notes

Reaction equation

HRID 2398792 reaction equation
[CH2:1]([OH:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].[H-].[Na+].Br[CH2:12][CH2:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20].CCOCC>COCCOC>[CH2:17]([O:16][CH2:15][CH2:14][CH2:13][CH2:12][O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:8])[CH2:18][CH:19]([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 123741,6-HexanediolHCID 24758Sodium hydrideHCID 214340651-(4-Bromobutoxy)-3-methylbutane

Product 1

HCID 214340426-(4-Isopentyloxybutyloxy)-hexanol

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

17.8 g (0.163 mol) of 1,6-hexandiol in 30 cc of absolute 1,2-dimethoxy ethane are added dropwise over the course of 15 minutes, under nitrogen and while stirring, to 4.85 g (0.117 mol) of 55% sodium hydride dispersion in oil, suspended in 140 cc of absolute 1,2-dimethoxy ethane. The mixture is stirred at 60° for 3 hours, 22.5 g (0.101 mol) of 1-bromo-4-isopentyloxy-butane are then added and then it is stirred at 60° for 40 hours. After cooling to 20°, 400 cc of ether are added to the reaction mixture. The ether solution is washed three times with water, subsequently with saturated sodium chloride solution, dried over sodium sulphate and evaporated. The residue is chromatographed with hexane/ethyl acetate (95:5) to (75:25) on silica gel. The almost pure fractions are fractionally distilled and 6-(4-isopentyloxy-butyloxy)-hexanol, having a B.P. of 134°-142°/0.5 mm Hg, is obtained as a colourless liquid.

Workup

  1. stirringit is stirred at 60° for 40 hours
  2. temperatureAfter cooling to 20°
  3. washThe ether solution is washed three times with water
  4. dry with materialsubsequently with saturated sodium chloride solution, dried over sodium sulphate
  5. customevaporated
  6. customThe residue is chromatographed with hexane/ethyl acetate (95:5) to (75:25) on silica gel
  7. distillationThe almost pure fractions are fractionally distilled
  8. customis obtained as a colourless liquid

Sources & evidence

ORD record
ord-63895d1a5ba24a45afd5c28535494e4b
Source dataset
uspto-grants-1977_05
Patent number
US04025641

Reaction notes

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