Water → HCID 86757620, compound

HRID 2267977Notes

Reaction equation

HRID 2267977 reaction equation
P(Cl)(Cl)(Cl)=O.C(O[CH:9]([O:16][CH2:17][CH3:18])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])C.[C:19](=O)([O-])[O-:20].[K+].[K+].O>CN(C)C=O.ClCCl>[CH2:17]([O:16][CH:9]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]#[CH:15])[CH:19]=[O:20])[CH3:18]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 69644Heptane, 1,1-diethoxy-

Product 1

HCID 86757620HCID 86757620, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

In 18.74 kg of dimethyl formamide (DMF) was added 11.48 kg of phosphorus oxychloride at 10° C., and stirred at the same temperature for 1 hour. To the sticky solution thus obtained was added 25 l of a solution of 6.0 kg (31.9 mol) of 1,1-diethoxyheptane in dichloromethane at 10° C., stirred at the same temperature for 2 hours, and then heated up to 70° C. in 30 min. The reaction solution was cooled down, gradually added to an aqueous solution of 33.2 kg of potassium carbonate and 100 l of water so that the temperature did not exceed 30° C., and then stirred at room temperature for 5 hours. The product was extracted with chloroform. The extract was washed with saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was distilled off under a reduced pressure, and the residue was purified by distillation to obtain 2.6 kg (15.3mol) of 2-ethoxymethylidenylheptanal. Yield of this product was 48%.

Workup

  1. customTo the sticky solution thus obtained
  2. stirringstirred at the same temperature for 2 hours
  3. temperatureThe reaction solution was cooled down
  4. customdid not exceed 30° C.
  5. stirringstirred at room temperature for 5 hours
  6. extractionThe product was extracted with chloroform
  7. washThe extract was washed with saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off under a reduced pressure
  10. distillationthe residue was purified by distillation

Sources & evidence

ORD record
ord-8f811b3e65d64b3bb43fda5423c0f6cf
Source dataset
uspto-grants-2001_12
Patent number
US06326065B1

Reaction notes

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