Acetic Acid → HCID 53954443, compound

HRID 1981476Notes

Reaction equation

HRID 1981476 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:13])[C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1.[H][H].C(O)(=O)C.[C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])(=[O:22])[CH3:21]>O>[CH3:3][N:4]([CH3:13])[C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[O:22])=[CH:7][CH:6]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 74794-(Dimethylamino)BenzaldehydeHCID 8164Octyl AcetateHCID 24758Sodium hydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 53954443HCID 53954443, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (1.9 g of an 80% dispersion in oil) was added portionwise with stirring over 0.5 hour to 4-dimethylaminobenzaldehyde (7.46 g) in 1-octyl acetate (158 g) at 25° C. The temperature was raised until a steady evolution of hydrogen was observed (40° C.) and held at this temperature for 48 hours. The cooled mixture was treated with glacial acetic acid (4 ml) and then water (50 ml) added. The upper layer was separated, washed with 10% sodium carbonate solution, water, and dried (MgSO4). The excess 1-octyl acetate was removed by distillation at 15 mm pressure. the residue solidified on cooling. It was crystallised from petroleum ether (B.P. 40°-60°) at 0° C., giving 14.2 g pale yellow crystals, m.p. 48°-49.5° C.

Workup

  1. custom(40° C.)
  2. customThe upper layer was separated
  3. washwashed with 10% sodium carbonate solution, water
  4. dry with materialdried (MgSO4)
  5. customThe excess 1-octyl acetate was removed by distillation at 15 mm pressure
  6. temperatureon cooling
  7. customIt was crystallised from petroleum ether (B.P. 40°-60°) at 0° C.

Sources & evidence

ORD record
ord-4e38d47174184020a52dbad2bfb02039
Source dataset
uspto-grants-1986_06
Patent number
US04592906

Reaction notes

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