2-Ethylbutyraldehyde → HCID 11789454, compound

HRID 484047Notes

Reaction equation

HRID 484047 reaction equation
CCN(CC)CC.[C:8]([O:12][C:13](=O)CC)(=[O:11])[CH2:9][CH3:10].CN([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22]N=1)C.C(C(CC)C=O)C>CCCCCC.O>[C:8]([O:12][CH:13]=[C:24]([CH2:25][CH3:20])[CH2:23][CH3:22])(=[O:11])[CH2:9][CH3:10]

Participants

7

Reactant 4

HCID 73592-EthylbutyraldehydeHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 31263Propionic anhydride

Product 1

HCID 11789454HCID 11789454, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Conditions

Temperature
70 °C

Procedure

A reaction vessel was charged sequentially with Et3N (12.8 L), propionic anhydride (14.48 L), dimethylaminopyridine (94 gm) and 2-ethylbutyraldehyde (7.5 L). The mixture was stirred and heated under gentle reflux (120°-135° C.) for 5 hours in a nitrogen atmosphere. The reaction was then cooled to 70° C. and H2O (13.5 L) was added slowly. On complete addition, the mixture was heated at reflux for 45 minutes and then cooled to room temperature before hexane (7.5 L) was added. The aqueous layer was separated and re-extracted with hexane (5 L) and the combined organic layers were washed with saturated NaHCO3 (2×7.5 L) before being evaporated in vacuo at 40° C. The residue (10 Kg) so obtained was fractionally distilled (b.p. 75°-80° C., 30-40 mm Hg) to give the required product (7.712 Kg) as a mobile liquid.

Workup

  1. temperatureheated
  2. temperatureunder gentle reflux (120°-135° C.) for 5 hours in a nitrogen atmosphere
  3. additionOn complete addition
  4. temperaturethe mixture was heated
  5. temperatureat reflux for 45 minutes
  6. additionwas added
  7. customThe aqueous layer was separated
  8. extractionre-extracted with hexane (5 L)
  9. washthe combined organic layers were washed with saturated NaHCO3 (2×7.5 L)
  10. custombefore being evaporated in vacuo at 40° C

Sources & evidence

ORD record
ord-2b7107e4e3fa436e9c9f00f73c4b15a4
Source dataset
uspto-grants-1993_07
Patent number
US05229381

Reaction notes

Loading…