1-Octanol → Acetaldehyde, (octyloxy)-

HRID 1395789Notes

Reaction equation

HRID 1395789 reaction equation
[CH2:1]([OH:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH-].[Na+].C[O:13][CH:14](OC)[CH2:15]Cl>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[CH2:1]([O:9][CH2:15][CH:14]=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 3

HCID 9571-OctanolHCID 14798Sodium HydroxideHCID 609862-Chloro-1,1-dimethoxyethane

Product 1

HCID 104512Acetaldehyde, (octyloxy)-Yield 50.6%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

A mixture of 130 grams of n-octanol, 60 grams of granular sodium hydroxide, 4 grams of Aliquat 336® (registered trademark of General Mills Chemicals, Inc.) and 110 grams of chloro acetaldehyde dimethyl acetal are heated to reflux for 4 hours. The reaction mass is cooled and 200 ml of water are added thereto with vigorous stirring. After all solids are dissolved, the aqueous phase is distilled to yield 87 grams of n-octanol (boiling point 60° C. at 1.4 mm Hg pressure) and 77 grams of n-octyl oxyacetaldehyde (boiling point 90° C. at 1.8 mm Hg). The conversion based on chloroacetaldehyde dimethyl acetal is 40% and the yield based on n-octanol is 83%.

Workup

  1. temperatureare heated
  2. temperatureto reflux for 4 hours
  3. temperatureThe reaction mass is cooled
  4. dissolutionAfter all solids are dissolved
  5. distillationthe aqueous phase is distilled

Sources & evidence

ORD record
ord-57e1168687bf497ebf6d155dad45cbd6
Source dataset
uspto-grants-1980_05
Patent number
US04205186

Reaction notes

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