Propanal → HCID 23322132, compound

HRID 280287Notes

Reaction equation

HRID 280287 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH:8](=O)[CH2:9]C.C(=O)([O-])[O-:13].[Na+].[Na+].Cl[CH2:19][Cl:20]>[Cl-].[Zn+2].[Cl-]>[CH3:3][C:2]([CH3:5])([CH3:4])[C:1]([O:6][CH:19]([Cl:20])[CH2:8][CH3:9])=[O:13]

Participants

6

Reactant 4

HCID 527PropanalHCID 6344Dichloromethane2×HCID 10340Sodium CarbonateHCID 62493Pivaloyl chloride

Product 1

HCID 23322132HCID 23322132, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

To a stirred solution of pivaloyl chloride (17.07 ml, 138.5 mmole) and zinc chloride (35 mg) in 50 ml of dry dichloromethane at 0° (ice bath) under nitrogen was added a solution of propionaldehyde (10 ml, 138.6 mmole) in 35 ml of dry dichloromethane portionwise (3 ml every 3 minutes). After the addition was complete, the solution was gradually warmed up to room temperature and stirred for 2 hours. The resulting solution was poured into a 10% sodium carbonate solution and extracted with pentane. The pentane extract was washed with brine, dried over anhydrous CaCl2, filtered and distilled. After the pentane distilled off, the residue was distilled in vacuum (5 mm Hg) to give 14 g of the title compound, b.p. 55°-60°, with consistent spectral data (H1 -NMR and C13 -NMR).

Workup

  1. additionAfter the addition
  2. extractionextracted with pentane
  3. extractionThe pentane extract
  4. washwas washed with brine
  5. dry with materialdried over anhydrous CaCl2
  6. filtrationfiltered
  7. distillationdistilled
  8. distillationAfter the pentane distilled off
  9. distillationthe residue was distilled in vacuum (5 mm Hg)

Sources & evidence

ORD record
ord-48d5647c270e450b9e90883ed6923847
Source dataset
uspto-grants-1986_05
Patent number
US04588743

Reaction notes

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