1-Hexanol → 1-(2,2-Diethoxyethoxy)hexane

HRID 1941058Notes

Reaction equation

HRID 1941058 reaction equation
[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Na+].[CH2:10]([O:12][CH:13]([O:16][CH2:17][CH3:18])[CH2:14]Br)[CH3:11]>C1(C)C=CC=CC=1>[CH2:10]([O:12][CH:13]([O:16][CH2:17][CH3:18])[CH2:14][O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH3:11]

Participants

5

Reactant 3

HCID 81031-HexanolHCID 24758Sodium hydrideHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 875351-(2,2-Diethoxyethoxy)hexaneYield 44.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Hexanol (200 g, 1.96 mol) and toluene (600 ml) were added to a 3 liter flask fitted with a mechanical stirrer and a reflux condenser. Sodium hydride (51.6 g, 2.15 mol) was added slowly to the resulting mixture, and then bromoacetaldehyde diethylacetal (385.7 g, 1.96 mol) was added dropwise. The mixture was heated to reflux temperature and maintained at that temperature for 6 hours. The mixture was then cooled to ambient temperature and was filtered to remove the resulting solids. Toluene was removed from the filtrate under reduced pressure, and the resulting product was distilled (85°-88° C.) to give 189.4 g of 2-hexyloxyacetaldehyde diethylacetal.

Workup

  1. customfitted with a mechanical stirrer and a reflux condenser
  2. temperatureThe mixture was heated
  3. temperatureto reflux temperature
  4. temperaturemaintained at that temperature for 6 hours
  5. filtrationwas filtered
  6. customto remove the resulting solids
  7. customToluene was removed from the filtrate under reduced pressure
  8. distillationthe resulting product was distilled (85°-88° C.)

Sources & evidence

ORD record
ord-bab3970c66424178970472e9670ab8ec
Source dataset
uspto-grants-1997_12
Patent number
US05702637

Reaction notes

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