Acetaldehyde → HCID 551339, compound

HRID 1589939Notes

Reaction equation

HRID 1589939 reaction equation
B(F)(F)F.[C:5]([O:10][C:11](=[O:15])[CH2:12]CC)(=[O:9])[CH2:6][CH2:7][CH3:8].[CH:16](=[O:18])[CH3:17].[C:19]([O-])(=O)[CH3:20].[Na+]>>[C:16]([O:15][CH:11]([O:10][C:5](=[O:9])[CH2:6][CH2:7][CH3:8])[CH3:12])(=[O:18])[CH2:17][CH2:19][CH3:20]

Participants

5

Reactant 4

HCID 177AcetaldehydeHCID 6356Boron trifluorideHCID 7798Butyric anhydrideHCID 517045Sodium Acetate

Product 1

HCID 551339HCID 551339, compound

Procedure

To ice-cooled BF3 -etherate (8.66 g.. 61 mmol.) is added dropwise via a syringe, over one hour, a mixture of butyric anhydride (6.58 g., 41.6 mmol.) and acetaldehyde (1.22 g., 27.7 mmol.). The reaction mixture is stirred for an additional 2 hours, 10% aq. sodium acetate solution (28 ml.) is added, and the mixture again stirred for 45 minutes. The oily layer is extracted into ether (2×25 ml.), and the combined ethereal extracts are washed with saturated aqueous sodium bicarbonate solution until no further evolution of CO2 is observed. The organic phase is then washed with water, dried over magnesium sulfate, filtered, concentrated and the residue is fractionally distilled at 8-12 mm. Hg, the fraction distilling at up to 62° C. being collected. Yield 2.18 g. (39%). 1H H-NMR ppm (CDCl3): 6.88 (q. J=5.6 Hz, 1H), 2.30 (dt, J=0.75, 7.5 Hz. 4H), 1.65 (sextet. J=7.5 Hz. 4H). 1.47 (d. J=5.5 Hz, 3H). 0.95 (t, J=7.5 Hz, 6H).

Workup

  1. additionis added dropwise via a syringe, over one hour
  2. stirringthe mixture again stirred for 45 minutes
  3. extractionThe oily layer is extracted into ether (2×25 ml.)
  4. washthe combined ethereal extracts are washed with saturated aqueous sodium bicarbonate solution until no further evolution of CO2
  5. washThe organic phase is then washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. distillationthe residue is fractionally distilled at 8-12 mm. Hg
  10. distillationthe fraction distilling at up to 62° C.
  11. custombeing collected

Sources & evidence

ORD record
ord-ad2f1024b09d473cb7096e38e91d5c7b
Source dataset
uspto-grants-1993_04
Patent number
US05200553

Reaction notes

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