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

HRID 1740685Notes

Reaction equation

HRID 1740685 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

2--Hexyloxyacetaldehyde diethylacetal was prepared as follows: 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. custom2--Hexyloxyacetaldehyde diethylacetal was prepared
  2. customfitted with a mechanical stirrer and a reflux condenser
  3. temperatureThe mixture was heated
  4. temperatureto reflux temperature
  5. temperaturemaintained at that temperature for 6 hours
  6. filtrationwas filtered
  7. customto remove the resulting solids
  8. customToluene was removed from the filtrate under reduced pressure
  9. distillationthe resulting product was distilled (85-88° C.)

Sources & evidence

ORD record
ord-45b8878ce248423a8aec9427b950ab6f
Source dataset
uspto-grants-1999_10
Patent number
US05972241

Reaction notes

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