Propanal → Propane, 1,1-diethoxy-

HRID 1987952Notes

Reaction equation

HRID 1987952 reaction equation
[CH:1]([O:8][CH2:9][CH3:10])([O:5][CH2:6][CH3:7])OCC.[CH2:11](O)[CH3:12].[N+]([O-])([O-])=O.[NH4+].C(=O)CC>C(=O)([O-])[O-].[Na+].[Na+]>[CH2:9]([O:8][CH:1]([O:5][CH2:6][CH3:7])[CH2:11][CH3:12])[CH3:10]

Participants

6

Reactant 4

HCID 527Propanal2×HCID 702EthanolHCID 22985Ammonium nitrateHCID 31214Ethyl orthoformate

Product 1

HCID 20858Propane, 1,1-diethoxy-Yield 93.8%

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Conditions

Temperature
33 °C

Procedure

Into a 2-liter flask under nitrogen were added 586 g (3.96 moles) of triethyl orthoformate, 46 g (56 ml, 1 mole) of ethanol, and 16 g of ammonium nitrate. Over the course of one hour 232 g (4 moles) of propionaldehyde were added with stirring. An ice bath was used as necessary to keep maintain the mixture at 30-36° C. The mixture turned yellow orange after one-third of the propionaldehyde had been added. The mixture was stirred overnight at room temperature and then brought to pH 7.5±0.2 with 10% aqueous sodium carbonate (about 30 ml). The aqueous layer was decanted, and the organic layer was distilled over sodium carbonate at atmospheric pressure to produce 124 g (81.6%) of 1.

Workup

  1. customAn ice bath was used
  2. additionhad been added
  3. stirringThe mixture was stirred overnight at room temperature
  4. customThe aqueous layer was decanted
  5. distillationthe organic layer was distilled over sodium carbonate at atmospheric pressure

Sources & evidence

ORD record
ord-4c397824d5c444778b17b70c2202d3aa
Source dataset
uspto-grants-2009_06
Patent number
US07553863B2

Reaction notes

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